BR112019007483A2 - 4-substituted phenylamine derivatives and their use to protect crops against undesirable phytopathogenic microorganisms - Google Patents

Abstract

This invention relates to 4-substituted phenylamine derivatives of the general formula (I), wherein r1 to r9 and a have the meanings defined in the description. The invention further relates to methods for its preparation and use of said compounds for combating undesirable phytopathogenic microorganisms, the agents for said purpose comprising said phenylamine derivatives all according to the invention. This invention further relates to a method for combating undesirable phytopathogenic microorganisms by applying said 4-substituted phenylamine derivatives of the general formula (I) to such undesirable microorganisms and / or their habitat according to the invention.

Description

“PHENYLAMINE 4-SUBSTITUTED DERIVATIVES AND THEIR USE TO PROTECT CROPS BY COMBATING UNDESIRABLE PHYTOPATHOGENIC MICRORGANISMS”

FIELD OF THE INVENTION [0001] The present invention relates to compounds intended to protect crops, combating unwanted phytopathogenic microorganisms. More precisely, the object of the present invention relates to substituted phenylamine 4 derivatives, used to protect cultures, combating unwanted phytopathogenic microorganisms.

BACKGROUND OF THE INVENTION [0002] The control of crop damage caused by phytopathogenic microorganisms is extremely important for achieving high crop efficiency. For example, damage caused by plant diseases in crops of ornamental plants, vegetables, cereal fields and fruit can cause a significant reduction in productivity and therefore result in increased costs for the consumer. There are many commercially available products for damage control. There is a continuing need for new compounds, which are more effective, less expensive, less toxic, environmentally safe and / or have different modes of action. Certain phenylamine derivatives are advertised in the literature as active microbicidal ingredients in pesticides. For example, the patents W02000046184, W02003093224, W02003024219, W02005089547 and W02005120234 disclose the use of phenylamine derivatives, especially phenylamidine, either alone or as part of a compound, as a fungicide. Certain phenylbenzamide compounds, the method of producing such compounds and their use for the control of undesirable microorganisms is disclosed in W02004005242.

[0003] US4173637 discloses phenylurea compounds and compositions that

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2/154 contain these compounds as insecticides. JP08291146 discloses N-substituted phenyl sulfonamide compounds with excellent herbicidal activity, especially as rice herbicides W02008110314 discloses fluoralkylphenylamidines as compound parasiticides, the method for their preparation and a method for protecting the seeds from unwanted microorganisms using these compounds. Another PCT publication WO2011095462 discloses phenylamine derivatives including carboxamides, the process for preparing them and the acaricidal, nematicidal or molluscidal compositions containing these derivatives.

[0004] The efficacy of the phenylamine derivatives described in the previous literature is good, but it falls short in several cases. Therefore, it is always of great interest in agriculture to use new pesticide compounds to prevent and / or control the development of microorganisms such as fungi, bacterial pathogens or pests that are resistant to known active ingredients. Therefore, it is of great interest to use new compounds that are more active than those already known, in order to decrease the amounts of active compounds to be used, while maintaining an efficiency, at least equivalent to that of already known compounds.

[0005] We have now come to a new family of compounds that have the effects or advantages mentioned above. A new family of compounds, that is, the substituted phenylamine 4 derivatives in which the phenyl ring is replaced according to the invention, thus allowing an unexpected and significantly greater activity against undesirable microorganisms, such as fungi or bacterial pathogens or pests.

SUMMARY OF THE INVENTION [0006] The present invention relates to substituted phenylamine 4 derivatives of the general formula (I)

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R ³ (I) where the definition of the substituents is defined in the detailed description above.

DETAILED DESCRIPTION OF THE INVENTION [0007] Accordingly, the present invention relates to compounds of general formula (I)

(D where it is selected from the group formed by hydrogen, CN, SR, S (O) _n R, OR, C1-2 alkyl, C1-2 alkoxy, C1-2 alkylthio, C2-i2-alkenyl, C2-i2-alkynyl, C1-12haloalkyl, C2-i2-haloalkenyl, C2-i2-haloalkynyl, Cs-s-cycloalkyl, C4-8cycloalkenyl, Cs-s-cycloalkynyl; where, in the cyclic ring system one or more carbon atoms can be substituted by heteroatoms selected from groups consisting of N, O, and S (O) _n ;

R ² and R ³ are independently selected from the group consisting of hydrogen, CN, S (O) _n R, OR ', (C = O) -R, C1-2 alkyl, C2-i2-alkenyl, C2-12alkynyl, C1-1-haloalkyl, C2-i2-haloalkenyl, C2-i2-haloalkynyl, Cs-s-cycloalkyl, C4-8-cycloalkenyl, Cs-s-cycloalkyl, Cs-is-aryl, Cj-i-aralkyl, Cy-i- caraway, where,

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4/154 in the cyclic ring system one or more carbon atoms can be replaced by hetero atoms selected from the groups consisting of N, O and S (O) _n ;

RI and R2, R2 and R3 or RI and R3 together with the atoms to which they are attached or together with other atoms selected from the group consisting of C (= O), C (= S), S (O) m and SiR'2 can form a four to seven-membered ring, which in turn can be replaced by one or more X, R ', OR', SR ', NR'2, SiR'3, COOR', CN, and CONR'2; and as a result, all groups of R1, R2, and R3 can be optionally substituted by one or more groups selected from the group consisting of X, R ', OR', SR ', NR'2, SiR' ₃ , COOR ', CN, and CONR '₂;

R ⁴ , R ⁵ , R ⁶ and R ⁷ are independently selected from the group consisting of hydrogen, X, CN, SCN, SF ₅ , S (O) _n R, SiR ' ₃ , OR, NRK, (C = O) - R, CR, NR, Ci_i2-alkyl, C2-i2-alkenyl, C2-i2-alkynyl, Ci_i2-haloalkyl, C2-12haloalcenilo, C2-I2 haloalkynyl, Ci_i2-haloalkoxy, Ci_i2-haloalkylthio, _C3 _8cicloalquilo, C4- 8-cycloalkenyl, Cs-s-cicloalquinil, _C3 _8-cycloalkyloxy, _C3 _8cicloalquiltio, Cs-is-aryl, Cy-IC-aralkyl, -C Ic-alkaryl; where, in the cyclic ring system, one or more carbon atoms can be replaced by hetero atoms selected from the groups consisting of N, O, and S (O) _n ; and all the groups mentioned above can be optionally substituted by one or more groups selected from the group consisting of X, R ', OR', SR ', NR'2, SiR' ₃ , COOR ', CN, and CONR'2; or where R ⁴ and R ⁷ or R ⁵ and R ⁶ together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from group consisting of C (= O), C (= S), S (O) _m and SiR'2 can form a four to seven-membered ring, which in turn can be replaced by one or more X, R ' , OR ', SR', NR ' ₂ , SíR' ₃ , COOR ', CN, and CONR'₂; and where all groups of R ⁴ , R ⁵ , R ⁶ and R ⁷ can optionally be replaced by one or more selected groups

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5/154 of the group consisting of X, R ', OR', SR ', NR' ₂ , SiR ' ₃ , COOR', CN, and CONR '₂; R ⁸ is selected from the group consisting of hydrogen, CN, SCN, S (O) _n R, SiR ' ₃ , NR'R, (C = O) -R, CR' = NR, Ci.i ₂ -alkyl , C ₂ _i ₂ -alkenyl, C ₂ _i ₂ -alkynyl, C1-1 ₂ -haloalkyl, C ₂ _i ₂ -haloalkenyl, C ₂ _i ₂ -haloalkynyl, C ₃ _8-cycloalkyl, C4-8cycloalkenyl, Cs-s-cycloalkynyl, Cs-is-aryl, C ₇ -9-aralkyl, C ₇ -o-alkaryl; where, in the cyclic ring system, one or more carbon atoms can be replaced by hetero atoms selected from the groups consisting of N, O, and S (O) _n ; and all of the groups mentioned above can be replaced by one or more groups selected from the group consisting of X, R ', OR', SR ', NR' ₂ , SiR ' ₃ , COOR', CN, and CONR '₂; Where

A is selected from the group consisting of fused or non-fused C-is-aryl, Cs-is-heteroaryl, where one or more carbon atoms are replaced by heteroatoms selected from N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) _m and SiR ' ₂ optionally substituted by one or more groups of R ⁹ ; Where

R ⁹ is selected from the group consisting of hydrogen, X, CN, SCN, SF5, R, OR, NO ₂ , NR ₂ , SíR ' ₃ , (C = O) -R, S (O) _n R, OS (O ) _n R, OSiR ' ₃ , NR'S (O) _n R, Ci_ ₈ -alkyl-S (O) _n R, Ci_ ₈ -alkyl- (C = O) -R, CR' = NR, S (O) _n C ₅ -i ₈ -aryl, S (O) _n C ₇ _ 19-aralkyl, S (O) _n C7-i9-alkaryl, C1-1 ₂ -alkyl, C ₂ _i ₂ -alkenyl, C ₂ _i ₂ -alkynyl, Ci_i ₂ haloalkyl, C ₂ -haloalcenilo _i _2, C _{2 2} _i -haloalquinil, Ci_i ₂ -alkoxy, -alkylthio Ci_i _2, i ₂ CI_ -holoalcóxi, Ci_i -haloalquiltio _2, _i ₂ C ₃ -cycloalkyl, C4-8- cycloalkenyl C5-8cicloalquinil, _C3 _8-cycloalkyloxy, _C3 _8-cycloalkylthio, C ₇ -i9-aralkyl, alkaryl C ₇ -i9-: bicyclic Cs-n-alkyl, Cj-n-alkenyl; where, in the cyclic ring system, one or more carbon atoms can be replaced by hetero atoms selected from the groups consisting of N, O, and S (O) _n ; and all of the groups mentioned above may be replaced by one or more groups selected from the group consisting of X, R ', OR', SR ', NR' ₂ , SiR ' ₃ , COOR', CN, and CONR '₂; or two

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R ⁹ together with the atoms to which they are attached can form a replaceable ring;

and where all groups of R ⁸ , R ⁹ and R ¹⁰ can be optionally substituted by one or more groups selected from the group consisting of X, R ', OR', SR ', NR' ₂ , SíR ' ₃ , COOR', CN, and CONR '₂;

Where

X represents halogen;

Where

R 'represents hydrogen, alkyl Ci_i ₂ straight chain or branched alkyl or Cs-io-cyclic alkyl which is optionally substituted by one or more X;

R represents hydrogen; NR _'2, OR', Ci_i ₂ straight chain or branched chain alkyl, Ci_i ₂ -haloalquil, _C3 _8-alkyl are cyclic, may optionally substituted one or more groups selected from the group consisting of X, R ', OR ', SR', NR ' ₂ , SíR' ₃ , COOR ', CN, and CONR' ₂ , C ₅ -i ₈ -aryl which is optionally substituted by one or more R ';

where men represent integrals where n = 0, 1 or 2; and m = 1 or 2.

[0008] According to another form of incorporation, the compounds of general formula (Ib) can also be described as

NYR ⁸ R ⁵ (Ib) where

R ^x and R ^y are independently selected from the group consisting of hydrogen, hydroxy, CN, NO ₂ , COOR ', S (O) _n R, OR', (C = O) -R, Ci_Ci ₂ -alkyl, C ₂ _i _2- alkenyl, C ₂ _i ₂ -alkynyl, C ₃ _8-cycloalkyl, C4-8-cycloalkenyl, C5-8

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7/154 cycloalkynyl, Cs-is-aryl, Cy-w-aralkyl, Cy-i-alkaryl; where, in the cyclic ring system, one or more carbon atoms can be replaced by hetero atoms selected from the groups consisting of N, O, and S (O) _n ; or

R ^x and R ^y together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) _m and SiR'2, can form a three to seven-membered ring, which in turn can be replaced by one or more X, R ', OR', SR ', NR'2, SiR' ₂ , COOR ', CN, and CONR'₂;

and where all other substituents R ⁴ to R ⁹ are as defined in the first embodiment.

[0009] In another preferred incorporation substitution, R ¹ of the compound of the general formula (I) is hydrogen, C1-2 alkyl, C1-2 alkyloxy, C1-12 alkylthio, C1-12 haloalkyl, Cs-s-cycloalkyl.

[0010] In another more preferred substitution embodiment, R ¹ of the compound of the general formula (I) is hydrogen, C 1-6 alkyl.

[0011] In another preferred incorporation substitution, R ² and R ³ of the compound of general formula (I) are C1-12 alkyl, C2-6 alkenyl, C2-12 alkynyl, C1-12 alkoxy, C1-12 alkylthio, C1-12 haloalkyl, Cs-s-cycloalkyl.

[0012] In another incorporation R ¹ and R ² , R ² and R ³ or R ¹ and R ³ together with the atoms to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) _m and SiR'2 can form a four to seven member ring, which, in turn, instead it can be replaced by one or more X, R ', OR', SR 'and CN.

[0013] In another preferred embodiment, the ring-forming structures with the substitutions R ¹ and R ² , R ² and R ³ or R ¹ and R ³ together with the atoms to which they are attached, are azetidine, pyrrolidine, imidazolidine , oxazolidine, piperidine,

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8/154 morpholino, thiomorpholino, piperazine, 1-methylpiperazine, 1-methylpyrrolidine, 1-methylpiperidine, 3-methyl-1,3-thiazinane.

[0014] In another preferred incorporation substitution, R ⁴ and R ⁵ of compound of general formula (I) are from X, CN, S (O) nR, NR'R, (C = O) -R, CR- NR, C i_i2 alkyl, C2-6 alkenyl ^{_, _} C 2-6 alkynyl, haloalkyl Ci_i2 ^{_, _} Ci_i2 haloalkylthio, C3-8 cycloalkyl, _C3 _8-cycloalkylthio.

[0015] In another preferred incorporation substitution, R ⁶ and R ⁷ of compound of general formula (I) are hydrogen, X, CN, S (O) _n R, NR'R, (C = O) -R , -NR COR, Ci_i2-alkyl, C2-6-alkenyl, C2-6-alkynyl, Ci_i2-haloalkyl, Ci_i2-haloalkylthio, _C3 _8 cycloalkyl, _C3 _8-cycloalkylthio.

[0016] In another preferred incorporation substitution, R ⁸ in the compound of general formula (I) is hydrogen, CN, S (O) _n R, NR'R, (C = O) -R, CR-NR, Ci_i2 alkyl, C2-6 alkenyl, C2-6 alkynyl, Ci_i2-haloalkyl, _C3 _scicloalquilo, _C3 _6-heterocyclyl, C ₃ _6-alkyl-heterocyclyl.

[0017] In another preferred incorporation substitution, R ⁹ in the compound of general formula (I) are X, CN, SCN, SF5, R, OR, NO2, NR'2, SiR ' ₃ , (C = O) - R, S (O) _n R, OS (O) _m R, OSiR _'3, -NR'S (O) _n R ₈ CI_-alkyl-S (O) _n R, Ci_8-alkyl- (C = O) -R , CR-NR, SCi_i2-alkyl, C2-i2-alkenyl, C2-i2-alkynyl, C1-12-haloalkyl, C2-i2-haloalkenyl, C1-1-alkoxy, C1-1-alkylthio, C1-2-holoalkoxy, C1-12-haloalkyl, C1-12-haloalkyl ₃ _i2 cycloalkyl, CZT-s-cycloalkenyl, _C3 _8-cycloalkyloxy, _C3 _scicloalquiltio.

[0018] In another embodiment two R ⁹ substitutions together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group which consists of C (= O), C (= S), S (O) _m and SiR '2 can form a four to ten membered ring, which in turn can be replaced by one or more X, R ', OR', SR ', NR'2, SiR' ₃ , COOR ', CN, and conr' ₂ .

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9/154 [0019] In another preferred embodiment A is phenyl, naphthalenyl, furyl, thienyl, pyrrolyl, thiazolyl, isoxazolyl, isothiazolyl, thiadiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinazolinyl, cin-nonyl; replaced by one or more R ⁹ .

[0020] In another embodiment A is phenyl, naphthalenyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl; replaced by one or more R ⁹ .

[0021] In another incorporation R ¹ to R ⁸ can still be optionally substituted by one or more groups selected from the groups consisting of X, R, OR ', SR', NR ' ₂ , SíR' ₃ , COOR ', CN, and CONR ' ₂ .

[0022] In another embodiment the preferred compound of the general formula (I) are:

N '- (2,5-dimethyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2,5-dimethyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimidamide;

N '- (2-chloro-5-methyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2,5-dimethyl-4- (N-phenyl-methyl-sulfonamide) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (2-methyl-4- (perfluoropropane-2-yl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide;

N '- (4 - ((4-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((3,4-dichlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

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Ν'- (2-chloro-5-methyl-4- (methyl (3,4,5-trifluorophenyl) amino) phenyl) -N-ethyl-N methylformimidamide;

N '- (2-chloro-5-methyl-4- (methyl (m-tolyl) amino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-4 - ((3,4-dichlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((3-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4- (methyl (4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4- (methyl (p-tolyl) amino) phenyl) -N-ethyl-N-methylformimidamide;

N '- (2-chloro-4 - ((2-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- (N-phenyl-methyl-sulfonamide) phenyl) -N-ethyl-N methylformimidamide;

N '- (2-chloro-4 - ((2-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((4-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((4-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((4-methoxy-3-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((3,4-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((3,5-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (m-tolyl) amino) phenyl) -N-ethyl-N-methylformimidamide;

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N-ethyl-N '- (4 - ((3-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (p-tolyl) amino) phenyl) -N-ethyl-N-methylformimidamide;

N-ethyl-N '- (4 - ((4-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide;

N-ethyl-N '- (4 - ((3-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimidamide;

N '- (2,5-dimethyl-4- (m-tolylamino) phenyl) -N-ethyl-N-methylformimidamide;

N '- (2,5-dimethyl-4- (p-tolylamino) phenyl) -N-ethyl-N-methylformimidamide;

N '- (4 - ((4- (tert-butyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((4- (tert-butyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((2-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((2-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimidamide;

N-ethyl-N '- (4 - ((2-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimidamide;

N-ethyl-N '- (4 - ((2-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide;

N '- (2-chloro-4 - ((2-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N-ethyl-N '- (4 - ((3-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide;

N-ethyl-N '- (4 - ((4-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide;

N '- (4 - ((2-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimidamide;

N- (4 - ((((ethyl) methyl) methylene) amino) -2,5-dimethylphenyl) -N-phenylacetamide;

N '- (2-chloro-5-methyl-4- (methyl (pyridin-2-yl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

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N '- (4 - ((4-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimidamide;

N-ethyl-N '- (4 - ((4-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimidamide;

N-ethyl-N '- (4 - ((2-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimidamide;

N-ethyl-N '- (4 - ((3-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimidamide;

N '- (2-chloro-4 - ((2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((3-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimidamide;

N- (3-chlorophenyl) -N, 2,5-trimethyl-4 - ((methylene morpholine) amino) aniline;

N '- (2-chloro-4 - ((3-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N- (3-chlorophenyl) -N, 2,5-trimethyl-4 - (((piperidine-1-yl-methylene) amino) aniline;

N-allyl-N '- (4 - ((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide;

N '- (4 - ((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-isopropyl-Nmethylformimidamide;

N '- (4 - ((2-bromophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimidamide;

N '- (4 - ((3-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimidamide;

N-ethyl-N '- (4 - ((4-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimidamide;

N '- (2,5-dimethyl-4 - ((2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

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N '- (2,5-dimethyl-4- (methyl (3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimidamide; N '- (4 - ((2-bromophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N-ethyl-N '- (4 - ((2-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (3- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- ((3 - (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4- (m-tolylamino) phenyl) -N-ethyl-N-methylformimidamide;

N '- (2-chloro-4 - ((3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- (o-tolylamino) phenyl) -N-ethyl-N-methylformimidamide;

N '- (2-chloro-4 - ((4-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimidamide;

N '- (2,5-dimethyl-4- (o-tolylamino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-4 - ((4-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4- (methyl (o-tolyl) amino) phenyl) -N-ethyl-N-methylformimidamide;

N '- (4 - ((2-bromophenyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((2-bromophenyl) (methyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (o-tolyl) amino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-4 - ((2-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

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Ν'- (2-chloro-5-methyl-4- ((2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4- (methyl (2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- ((4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((3-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((4-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((3-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((4-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- ((3 - (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4- (methyl (3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((2,6-difluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-4 - ((2,6-difluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((2,6-difluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

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N '- (2-chloro-4 - ((2,6-difluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((2-chloro-6-fluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((2-chloro-6-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((2-chloro-6-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((4- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((2,6-dichloro-4- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- ((3 - (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- ((4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- (methyl (2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

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N '- (2-chloro-5-methyl-4- (methyl (4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- (methyl (3 - (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- (N-phenylethylsulfonamido) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((2,4-dichloro-6- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4 - (((4- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((2-chloro-6-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (4- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4- (methyl (4- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide;

N '- (2-chloro-5-methyl-4- (methyl (3- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((2 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- ((2- ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N methylformimidamide;

N '- (4 - ((3 - ((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((4 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- ((4- ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N methylformimidamide;

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N- (2,5-dimethyl-4- (methyl (2 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N- (2-chloro-5-methyl-4- (methyl (2 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N- (2,5-dimethyl-4- (methyl (4 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N- (2-chloro-5-methyl-4- (methyl (4 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N- (4 - ((3 - ((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((3 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimidamide;

N '- (2-chloro-5-methyl-4 - ((4- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N- (2,5-dimethyl-4- (methyl (3 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N- (2-chloro-5-methyl-4- (methyl (3 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (4- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4- (methyl (4- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((3- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4 - (((3- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

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N '- (2,5-dimethyl-4- (methyl (3- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4- (methyl (3- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide;

N '- (4 - ((3,5-bis (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((3,5-bis (trifluoromethyl) phenyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- ((3 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N methylformimidamide;

N '- (2-chloro-4 - ((4- (dimethylamino) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((4- (dimethylamino) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((3 - ((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((3 - ((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethylN-methylformimidamide;

N '- (4 - ((3- (difluoromethoxy) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((3- (difluoromethoxy) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((3- (difluoromethoxy) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

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N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((4- (difluoromethoxy) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((2,5-difluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-4 - ((2,5-difluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((3,5-bis (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((3,5-bis (trifluoromethyl) phenyl) (methyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dbnetyl-4 - ((5-methyl-2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (4 - ((2,5-difluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N methylformimidamide;

N '- (2-chloro-4 - ((2,5-difluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (5-methyl-2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((4-chloro-2- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((4-chloro-2- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (4 - ((4-chloro-2- (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N methylformimidamide;

N '- (2-chloro-4 - ((4-chloro-2- (trifluoromethyl) phenyl) (methyl) amino) -5-methylphenyl) -Netyl-N-methylformimidamide;

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N '- (2-chloro-5-methyl-4- (methyl (2- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((3- (difluoromethoxy) phenyl) (methyl) ammo) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- ((2- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((2-chloro-4- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((2-chloro-4- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (4 - ((2-chloro-4- (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N methylformimidamide;

N '- (2-chloro-4 - ((2-chloro-4- (trifluoromethyl) phenyl) (methyl) amino) -5-methylphenyl) -Netyl-N-methylformimidamide;

N '- (2,5-dimethyl-4 - ((2- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimidamide;

N-ethyl-N'- (4- ((4-fluoro-3 - (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -2,5-dimethylphenyl) N-methylformimidamide;

N '- (2-chloro-4 - ((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -5-methylphenyl) N-ethyl-N-methylformimidamide; 5-chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4 - ((methylene morpholine) amino) aniline;

N '- (2-chloro-4- (N- (2-fluorophenyl) methylsulfonamido) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2 fluorophenyl) acetamide;

N '- (2-chloro-4 - ((2-fluorophenyl) (methyl) amino) -5-methylphenyl) -N, Ndimethylformimidamide;

N '- (2-chloro-4- (ethyl (2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

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5-chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4 - ((methylene morpholine) amino) aniline; 5-chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4 - (((thio-methylene morpholine) amino) aniline;

N-ethyl-N '- (5-fluoro-4 - (((4-fluoro-3- (1,1, 2,2-tetrafluoroethoxy) phenyl) amino) -2methylphenyl) -N-methylformimidamide;

N-ethyl-N '- (5-fluoro-4 - ((4-fluoro-3- (1,1, 2,2-tetrafluoroethoxy) phenyl) (methyl) amino) -

2-methylphenyl) -N-methylformimidamide;

N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2chlorophenyl) acetamide;

N '- (2-chloro-4- (N- (2-chlorophenyl) methylsulfonamido) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((4 - ((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((4 - ((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((4 - ((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((4 - ((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethylN-methylformimidamide;

N '- (2-chloro-4- (ethyl (phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimidamide;

N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -Nphenylacetamide;

N '- (2-chloro-4 - ((2 - ((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((2 - ((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethylN-methylformimidamide;

N '- (2-chloro-4- (ethyl (3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

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N '- (2-chloro-4 - ((3- (difluoromethoxy) -4-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-4- (N- (3-methoxyphenyl) methylsulfonamido) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((3- (difluoromethoxy) -4-fluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-4 - ((3- (difluoromethoxy) -4-fluorophenyl) (methyl) amino) -5-methylphenyl) -Netyl-N-methylformimidamide;

N '- (4 - ((3- (difluoromethoxy) -4-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethylN-methylformimidamide;

N '- (4 - ((2,5-dimethylphenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-4 - ((2,5-dimethylphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2chlorophenyl) propionamide;

N-ethyl-N '- (5-fluoro-4 - ((4-methoxyphenyl) amino) -2-methylphenyl) -Nmethylformimidamide;

N-ethyl-N '- (5-fluoro-4 - ((4-methoxyphenyl) (methyl) amino) -2-methylphenyl) -Nmethylformimidamide;

N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2fluorophenyl) propionamide

N '- (2-chloro-4- (N- (4-fluoro-3- (1,1, 2,2-tetrafluoroethoxy) phenyl) methylsulfonamido) 5-methylphenyl) -N-ethyl-N-methylformimidamide;

N '- (2,5-dimethyl-4 - ((3- (1,1, 2,2-tetrafluoroethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2,5-dimethyl-4- (methyl (3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

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N-ethyl-N '- (4 - ((2-fluoro-5-methylphenyl) anüno) -2,5-dimethylphenyl) -Nmethylformimidamide;

N-ethyl-N '- (5-fluoro-4 - ((2-fluorophenyl) anüno) -2-methylphenyl) -Nmethylformimidamide;

N-ethyl-N '- (4 - ((2-fluoro-5-methylphenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide;

N '- (2-chloro-4 - ((2-fluoro-5-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N-ethyl-N '- (5-fluoro-2-methyl-4- (phenylamino) phenyl) -N-methylformimidamide; N '- (4 - ((2-chlorophenyl) anüno) -5-fluoro-2-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((4- (tert-butyl) phenyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-Nmethylformimidamide;

N-ethyl-N '- (5-fluoro-2-methyl-4- (m-tolylammo) phenyl) -N-methylformimidamide;

N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -Nphenylpropionamide;

N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (3methoxyphenyl) acetamide

N '- (2-chloro-4 - (((4-fluoro-3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N-ethyl-N '- (4 - ((4-fluoro-3-methoxyphenyl) anno) -2,5-dimethylphenyl) -Nmethylformimidamide;

N-ethyl-N '- (4 - ((4-fluoro-3-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide;

N '- (4 - ((2 - ((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (4 - ((2 - ((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide;

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N '- (2-chloro-4 - ((4-fluoro-3-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-bromo-6-fluoro-3-methyl-4- (phenylamino) phenyl) -N-ethyl-Nmethylformimidamide;

N '- (2-chloro-5-methyl-4 - (((5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl) amino) phenyl) -Netyl-N-methylformimidamide;

N '- (2-bromo-6-fluoro-3-methyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

Ν'- (2-chloro-5-methyl-4- ((1-methylindoline-5-yl) amino) phenyl) -N-ethyl-N methylformimidamide;

N '- (2,5-dimethyl-4 - (((5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl) amino) phenyl) -N-ethyl-Nmethylformimidamide;

N-ethyl-N '- (5-fluoro-2-methyl-4- (methyl (phenyl) amino) phenyl) -N-methylformimidamide; N '- (4 - ((4- (tert-butyl) phenyl) (methyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-Nmethylformimidamide;

N-ethyl-N '- (5-fluoro-2-methyl-4- (methyl (m-tolyl) amino) phenyl) -Nmethylformimidamide;

N-ethyl-N '- (7 - ((2-methoxyphenyl) amino) -2,3-dihydro-1H-indeno-4-yl) -Nmethylformimidamide;

N-ethyl-N-methyl-N '- (7- (p-tolylamino) -2,3-dihydro-1H-indeno-4-yl) formimidamide;

N '- (7 - ((4-chlorophenyl) amino) -2,3-dihydro-1H-indeno-4-yl) -N-ethyl-Nmethylformimidamide;

N-ethyl-N-methyl-N '- (4- (phenylamino) naphthalene-1-yl) formimidamide;

N '- (2,5-dimethyl-4- (pyridine-2-ylamino) phenyl) -N-ethyl-N-methylformimidamide;

N '- (2,5-dimethyl-4- (methyl (pyridin-2-yl) amino) phenyl) -N-ethyl-N-methylformimidamide and

Ν'- (2-chloro-5-methyl-4- (pyridine-2-ylamino) phenyl) -N-ethyl-N-methylformimidamide;

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25/154 * Names of the compounds generated using Chemdraw Professional 16.0 [0023] Any of the compounds according to the invention can exist in one or more optical, geometric, or chiral isomers depending on the number of asymmetric centers in the compound. The invention thus relates equally to all optical isomers and their racemic or scalemic mixtures (the term scalemic denotes a mixture of enantiomers in different proportions), and mixtures of all possible stereoisomers, in all proportions. The diastereoisomers and / or the optical isomers can be separated according to methods which are known per se by a normal person skilled in the art.

Any of the compounds according to the invention can also exist in one or more geometric isomeric forms depending on the number of asymmetric centers in the compound. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions. Geometric isomers can be separated according to methods that are known per se to a normal person skilled in the art.

[0025] Any of the compounds according to the invention, can also exist in one or more amorphic or isomorphic or polymorphic forms, depending on their preparation, purification and storage and several other factors. The invention thus relates to all amorphic, isomorphic and polymorphic forms, in all proportions. The amorphic, isomorphic and polymorphic forms can be prepared and / or separated and / or purified, according to general methods which are known per se by a normal person skilled in the art.

[0026] In the above description, the term alkyl, used alone or in compound words such as alkylthio, or haloalkyl includes straight or branched alkyl chair, such as methyl, ethyl, n-propyl, iso-propyl, or the different isomers butyl, pentyl or hexyl.

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26/154 [0027] Alkenyl includes straight or branched chain alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1, 2propadiene and 2,4-hexadiene.

[0028] Alquinyl includes straight or branched chain alkynes, such as ethynyl, 1-propynyl, 2-propynyl and the different butinyl, pentynyl and hexynyl isomers. Alkynyl can also include halves composed of several multiple links such as 2,5-hexadinyl.

[0029] Cycloalkyl or cycloalkyl includes, for example, cyclopropyl cyclobutyl, cyclopentyl, and cyclohexyl. Cycloalkenyl includes, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl. Cycloalkynyl, likewise, refers to cyclic pentynyl, hexynyl, heptinyl and octinyl.

[0030] Cycloalkyloxy includes, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy.

[0031] Cycloalkylthio, includes, for example, cyclopropylthio, cyclobutylthio, cyclopentylthio.

[0032] The term "aryl" used here is a group that contains any carbon-based aromatic group, including, but not limited to, phenyl, naphthalene, biphenyl, anthracene and the like. The aryl group can be substituted or unsubstituted. In addition, the aryl group can be a single ring structure or include several ring structures which are either fused ring structures or linked through one or more bridge groups, such as a carbonocarbon bond.

[0033] The term aralkyl refers to aryl hydrocarbon radicals including an alkyl moiety, as defined above. Examples include benzyl, phenylethyl and 6-naphthylhexyl. As used herein, the term aralkenyl refers to aryl hydrocarbon radicals, including a portion of alkenyl, as defined above, and a portion of aryl, as

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27/154 defined above. Examples include styryl, 3- (benzyl) prop-2-enyl, and 6naphthylhex-2-enyl.

[0034] The term alkaryl refers to an aryl group that contains an alkyl group; According to what is used here the term alkaryl includes substituted and unsubstituted groups. An example of an alkaryl group is the radical 4methylphenyl.

[0035] Alkoxy includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.

[0036] Alkylthio, includes straight or branched chain alkylthio, halves such as methylthio, ethylthio, and the different isomers propylthio, butylthio, pentylthio and hexylthio.

[0037] The term hetero in connection with the rings refers to a ring in which at least one atom of the ring is not carbon and which may contain 1 to 4 hetero atoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygen and no more than 2 sulfur.

[0038] The term heterocycle refers to a cyclic ring system in which at least one ring atom is not carbon and which may contain heteroatoms independently selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus, boron etc.

[0039] The term heterocycle can further be classified as non-aromatic heterocycle and aromatic or heteroaryl heterocycle.

[0040] The term non-aromatic heretocycle ”includes a fused or non-fused monocyclic or polycyclic heterocycle of three to fifteen members, preferably three to twelve members, saturated or completely or partially unsaturated, (spiro, fused, bridged , non-fused) where the heteroatom is selected from the group of oxygen, nitrogen and sulfur; and, if the ring contains more than one oxygen atom, they are not directly

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Adjacent 28/154; Non-limiting examples of non-aromatic heterocycle include oxetanil, oxiranil; aziridinyl; thyranyl, azetidinyl, tietanyl, dithietanyl, diazetidinyl, 2-tetrahydrofuranyl; 3-tetrahydrofuranyl; 2-tetrahydro-thienyl; 3-tetrahydro-thienyl; 2-pyrrolidinyl; 3-pyrrolidinyl; 3-isoxazolidinyl; 4isoxazolidinyl; 5-isoxazolidinyl; 3-isothiazolidinyl; 4-isothiazolidinyl; 2-tetrahydropyranyl; 4-tetrahydropyranyl; This definition also applies to heterocyclic as part of a substituent, for example, alkylheterocyclic (heterocyclic radicals, including an alkyl moiety as defined above), etc., unless specifically defined otherwise.

[0041] The term heteroarylaryl, as used herein, is a group containing a monocyclic or polycyclic unsaturated fused or unfused ring system of three to fifteen members, preferably with three to twelve members, more preferably still of 5 or 6 limbs, containing heteroatoms selected from oxygen, nitrogen, sulfur, phosphorus, boron, etc. Non-limiting examples of 5-membered heteroaryl groups include 2-furyl; 3-furyl; 2- thienyl; 3-thienyl; 2-pyrrolyl; 3-pyrrolyl; 3isoxazolyl; 4-isoxazolyl; 5-isoxazolyl; 3-isothiazolyl; 4-isothiazolyl; 5 isothiazolyl; 3-pyrazolyl; 4-pyrazolyl; 5-pyrazolyl; 2-oxazolyl; 4-oxazolyl; 5oxazolyl; 2-thiazolyl; 4-thiazolyl; 5-thiazolyl; 2-imidazolyl; 4-imidazolyl; 1,2,4-oxadiazol-3-yl; 1,2,4-oxadiazol-5-yl; 1,2,4-thiadiazol-3-yl; 1,2,4-thiadiazole-5yl; 1,2,4-triazol-3-yl; 1,4,4-oxadiazol-2-yl; 1, 3,4-thiadiazol-2-yl and 1, 3,4-triazole-

2-yl; 1-pyrrolyl; 1-pyrazolyl; 1,2,4-triazol-1-yl; 1-imidazolyl; 1,2,3-triazol-lilo; 1,3,4-triazol-1-yl and the like.

Non-limiting examples of 6-membered heteroaryl groups include 2-pyridinyl; 3-pyridinyl; 4-pyridinyl; 3-pyridazinyl; 4-pyridazinyl; 2 pyrimidinyl; 4-pyrimidinyl; 5-pyrimidinyl; 2-pyrazinyl; 1, 3,5-triazine-2-yl; 1,

2,4-triazine-3-yl; 1, 2,4,5-tetrazine-3-yl and the like.

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29/154 [0044] Non-limiting examples of 5-membered benzofused heteroaryl include indol-1-yl; indol-2-yl; indol-3-yl; indol-4-yl; indol-5-yl; indole-6-yl; indol-7-yl; benzimidazol-1-yl; benzimidazol-2-yl; benzimidazol-4-yl; benzimidazol-5-yl; indazol-1-yl; indazol-3-yl; indazol-4-yl; indazol-5-yl; indazol-6-yl; indazol-7-yl; indazol-2-yl; 1-benzofuran-2-yl; 1-benzofuran-3yl; 1-benzofuran-4-yl; 1-benzofuran-5-yl; 1-benzofuran-6-yl; 1benzofuran-7-yl; 1-benzothiophene-2-yl; 1-benzothiophene-3-yl; 1-benzothiophene-4yl; 1-benzothiophene-5-yl; 1-benzothiophene-6-yl; 1-benzothiophene-7-yl; 1,3benzothiazol-2-yl; 1,3-benzothiazol-4-yl; 1,3-benzothiazol-5-yl; 1,3-benzothiazol6-yl; 1,3-benzothiazol-7-yl; 1,3-benzoxazol-2-yl; 1,3-benzoxazol-4-yl; 1,3benzoxazol-5-yl; 1,3-benzoxazol-6-yl; 1,3-benzoxazol-7-yl and the like.

Non-limiting examples of 6-membered benzofused heteroaryl include quinoline-2-yl; quinoline-3-yl; quinoline-4-yl; quinoline-5-yl; quinoline-6-yl; quinoline-7-yl; quinoline-8-yl; isoquinoline-1-yl; isoquinoline-

3-yl; isoquinoline-4-yl; isoquinoline-5-yl; isoquinoline-6-yl; isoquinoline-7yl; isoquinoline-8-yl and the like.

[0046] The term halogen, alone or in compound words like haloalkyl, includes fluorine, chlorine, bromine and iodine. In addition, when used in compound words like haloalkyl, said alkyl can be partially or totally replaced by halogen atoms that can be the same or different. Non-limiting examples of haloalkyl include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2,2-fluoroethyl, 2,2 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,

2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2trifluoroethyl and 1,1,1-trifluoroprop-2-yl.

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[0047] The terms haloalkenyl, haloalkynyl, haloalkoxy, haloalkylthio, are defined analogously, except that, instead of alkyl groups, alkenyl, alkynyl, alkoxy and alkylthio groups are present as a part of the substituent.

[0048] The total number of carbon atoms in a substituent group is indicated by Ci-j, where the prefix i and j are numbers from 1 to 21. For example, Ci-3 alkoxy designates methoxy through propoxy. In the above recitations, when a compound of Formula I is composed of one or more heterocyclic rings, all substituents are attached to these rings through any carbon or nitrogen available by replacing a hydrogen with said carbon or nitrogen.

[0049] When a compound is substituted with a substituent bearing an exponent that indicates that the number of said substituents may exceed 1, said substituents (when they exceed 1) are selected regardless of the group of the defined substituents. In addition, when the subscript indicates a range, for example (R) i_j, then the number of substituents can be selected from the integers between i and j, inclusive.

[0050] When a group contains a substituent that may be hydrogen, for example, R ¹ or R ² , then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to that group being unsubstituted.

[0051] The present invention also relates to a composition for the control of undesirable microorganisms, comprising at least one of the compounds of the formula (I) and one or more inert vehicles. The inert vehicle also includes agronomically suitable auxiliaries, solvents, thinners, surfactants and / or thinners and the like.

[0052] The present invention also relates to a composition for the control of undesirable microorganisms, including at least one of the

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31/154 compounds of the formula (I) and / or one or more compatible active compounds selected from fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, biopesticides, growth regulators, antibiotics, fertilizers and / or mixtures thereof.

[0053] The present invention also relates to a composition where the concentration of compounds of the general formula (I) varies from 1 to 90% by weight, in relation to the total weight of the composition, preferably from 5 to 50% in weight in relation to the total weight of the composition.

[0054] The present invention also relates to a method for controlling undesirable microorganisms, where the compounds of formula (I) are applied to the microorganisms and / or their habitat.

[0055] The present invention provides an additional method for protecting seeds against unwanted microorganisms using seeds treated with at least one compound of formula (I).

[0056] The compounds of formula (I) can have potent microbicidal activity and can be used for the control of undesirable microorganisms, such as fungi, insects, mites, nematodes and bacteria, in the protection of agricultural or horticultural crops and in the protection of such materials.

[0057] The compounds of formula (I) can have very good fungicidal properties and can be used in crop protection, for example, to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

[0058] The compounds of formula (I) can be used as nematicides in crop protection, for example, to control Rhabditida, Dorylaimida and Tryplonchida.

[0059] The compounds of formula (I) can be used as insecticides in crop protection, for example, to control Lepidoptera, Coleoptera, Hemiptera, Homoptera, Thysanoptera, Diptera, Coleoptera and Isoptera.

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32/154 [0060] The compounds of formula (I) can be used as acaricides in crop protection, for example, to control Eriophyoidea, Tetranychoidea, Eupodoidea and Tarsonemidae.

[0061] The compounds of formula (I) can be used as bactericides in crop protection, for example, for the control of Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

[0062] The compounds of formula (I) can be used as herbicides and can be effective against a broad spectrum of economically important mono- and dicotyledonous harmful plants. The monocot weed species may include Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus species from the annual group and perennial species of Agropyron, Cynodon, Imperata and Sorghum and also perennial species of Cyperus. The broadleaf dicotyledonous species can include Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon on the annual side, and also Convolvulus, Cirsium, Rumex and Artemisia in the case of perennial weeds of wide leaf. Harmful plants can occur in rice, as, for example, in Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus, and can be controlled by the compounds of formula (I).

[0063] The compounds of formula (I) can be used for curative control or protection of phytopathogenic fungi. Therefore, the invention also refers to curative and protective methods for the control of phytopathogenic fungi through the use of creative active ingredients or compositions, which are applied to the seeds, plants or parts of the plant, the fruit or the soil in which the plants grow.

[0064] The compounds of formula (I) can be used to control or prevent phytopathogenic fungi, bacteria, insects, nematodes, mites from agricultural crops and / or horticultural crops.

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33/154 [0065] The compounds of formula (I) can be used in crop protection, where agricultural crops are cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, nuts trees and citrus and citrus trees, any vegetable plants, cucurbitaceae, oil plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potatoes, tomatoes, onions, peppers and other vegetables and ornamentals.

[0066] According to the invention, as defined above, a vehicle is a natural or synthetic, organic or inorganic substance with which the active ingredients are mixed or combined for better applicability, in particular for application to plants or parts of plants or seeds. The vehicle, which can be solid or liquid, is generally inert and must be suitable for use in agriculture.

[0067] Useful solid vehicles include, for example, ammonium salts and natural rock flours, such as kaolin, clays, talc, chalk, quartz, atapulgite, montmorillonite or diatomaceous earth, and synthetic rock flours, such as finely divided silica , alumina and silicates; solid vehicles useful for granules include: for example, crushed and fractionated natural stones such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules from organic and inorganic flours, and granules from organic materials such as paper, sawdust, coconut husks, corn cobs and tobacco stalks; useful emulsifiers and / or foams include: for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, arylsulfonates and also protein hydrolysates; suitable dispersants are nonionic and ionic substances, for example, from the classes of alcohol ethers-POE and / or -POP, acid ethers and / or POP POE, alkylaryl ethers and / or POP POE, adductors of

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34/154 fat and / or POP POE, derivatives of POE and / or POP-polyol, adductors of POE and / or POP-sorbitan or -sugar, alkyl or aryl sulfates, alkyl or aryl sulfonates and alkyl or aryl phosphates or the corresponding PO-ether adductors. In addition, oligo- or polymers, for example, derivatives of vinyl monomers, acrylic acid, EO and / or PO, alone or in combination with, for example, (poly) alcohols or (poly) amines are suitable. It is also possible to use lignin and its derivatives of sulfonic acid, modified and unmodified celluloses, aromatic and / or aliphatic sulfonic acids and also their adducts with formaldehyde.

[0068] The active ingredients can be applied as such or converted to the usual formulations or in the form of their formulations or using forms prepared from them, such as ready-to-use solutions, emulsions, water-based or water-based suspensions oil, powders, wettable powders, pastes, soluble powders, soluble tablets, dust, soluble granules, granules for diffusion, suspoemulsion concentrates, natural products impregnated with the active ingredient, synthetic substances impregnated with the active ingredient, fertilizers and also microencapsulations in polymeric substances . The application is carried out in the usual way, for example, by watering, spraying, atomizing, nursery boxes, diffusion, dust spreading, foam spreading, spraying and the like. It is also possible to implant the active ingredients using the ultra-low volume method or inject the active ingredient preparation or the ingredient itself into the soil. It is also possible to treat plant seeds.

[0069] The active ingredients can be converted into a nanoformulation with the intention of improving water solubility, thermal stability, bioavailability, sensory attributes and physiological performance.

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35/154 [0070] In addition, the choice of type of formulation will depend on the specific use.

[0071] The mentioned formulations can be prepared in a manner known per se, for example, by mixing the active ingredients with at least one usual extender, solvent or diluent, emulsifier, dispersant and / or binding or fixing agent, a wetting agent, water repellent, or, if applicable, UV drying and stabilizers and, if necessary, dyes and pigments, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also other processing aids.

[0072] The present invention includes not only formulations that are already ready for use and that can be implanted with a suitable device, in the plant or in the seed, but also commercial concentrates that have to be diluted in water before use.

[0073] The auxiliaries used can be those substances that are suitable for imparting particular properties to the composition itself and / or to the preparations derived therefrom (for example, spray liquors, dressings for seeds), such as certain technical properties and / or also specific biological properties. Typical auxiliaries include extenders, solvents and vehicles.

[0074] Suitable extenders are, for example, water, polar and non-polar organic chemical liquids, for example, from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which can also optionally be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (including oils and fats) and (poly) ethers, substituted and unsubstituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).

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36/154 [0075] Liquefied gas extenders or vehicles are understood as liquid media that are gaseous at standard temperature and under normal pressure, for example, aerosol propellants, such as halo-hydrocarbons, or else butane, propane, nitrogen and carbon dioxide.

[0076] In the formulations it is possible to use adhesion agents such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latexes, such as arabica, polyvinyl alcohol and polyvinyl acetate, or else the natural phospholipids such such as cephalins and lecithins and synthetic phospholipids. Still other additives can be mineral, vegetable oils and methylated seed oils.

[0077] If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Useful liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, dormatic aromatics or dormant aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example fractions of petroleum, alcohols such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, or else Water.

[0078] Compositions comprising compounds of formula (I) may additionally include new elements, for example, surfactants. Suitable surfactants are emulsifiers and / or foaming agents, dispersing or wetting agents, with ionic and non-ionic properties, or mixtures of these surfactants. Examples of this are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably

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37/154 alkylphenols or arylphenols), salts of sulfosuccinic esters, derivatives of taurine (preferably alkyl taurates), phosphoric esters of alcohols or polyethoxylated phenols, fatty esters of polyols and derivatives of compounds containing sulphates, sulphates and phosphates, for example alkylarylpolyglycolic ethers, alkylsulfonates, alkylsulfates, arylsulfonates, protein hydrolysates, lignosulphite residual liquors and methylcellulose. The presence of a surfactant is necessary if one of the active ingredients and / or one of the inert vehicles is insoluble in water and when the application is made in water. The proportion of surfactants is between 5 and 40 percent by weight of the composition of the invention.

[0079] It is possible to use dyes, inorganic pigments, such as, for example, iron oxide, titanium oxide and Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and metallic phthalocyanine dyes, and micronutrients like salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

[0080] Still other additives can be perfumes, minerals or vegetables, optionally modified oils, waxes and nutrients (including micronutrients), such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts.

[0081] Additional components can be stabilizers, such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical agents that improve chemical and / or physical stability.

[0082] If necessary, other additional components may also be present, for example, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestering agents, complexing agents. In general, the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.

[0083] Formulations generally contain between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, plus

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38/154 preferably still between 0.5 and 90% of active ingredient, and most preferably between 10 and 70% by weight.

[0084] The formulations described above can be used to control unwanted microorganisms, wherein the compositions comprising compounds of formula (I) are applied to the microorganisms and / or their habitat.

[0085] The compounds of formula (I) according to the present invention, as well as salts, N-oxides, metal complexes, stereoisomers or polymorphs can be used as such or in formulations thereof and can be mixed with the known mixing partners in order to expand, for example, the spectrum of activity or to prevent the development of resistance. Useful mixing partners include, for example, fungicides, insecticides, acaricides, nematicides, biopesticides and bactericides. A mixture with other active ingredients, such as herbicides, or with fertilizers and growth regulators, phytoprotectors and / or semi-chemicals, is also possible.

[0086] Examples of such chemical ingredients are given here, but not in a limiting way. Some of them are specified here by their common names, as they are known and described, for example, in The Pesticide Manual 17th Ed., Or can be searched on the Internet (for example, at www.alanwood.net/pesticides). Others are designated by their systematic name following IUPAC's nomenclature rules.

[0087] All designated mixing partners of classes (A) to (O), as described below, may, if their functional groups provide it, optionally form salts with suitable acids or bases, appear as stereoisomers, even if they are not specifically mentioned in each case, or as polymorphs. They are also understood to be included in this document. These examples are

A) Ergosterol biosynthesis inhibitors, for example (A01) aldimorph,

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39/154 (A02) azaconazole, (A03) bitertanol, (A04) bromuconazole, (A05) cyproconazole, (A06) diclobutrazol, (A07) diphenoconazole, (A08) diniconazole, (A09) diniconazole-M, (A10) dodemorfo, (All) dodemoryl acetate, (A12) epoxiconazole, (Al3) etaconazole, (A 14) fenarimol, (Al5) fenbuconazole, (Al6) fenhexamide, (A17) phenpropidine, (A18) fenpropimorfo, (A19) fluquinconazole, (A20) flurprimidol, (A21) flusilazole, (A22) flutriafol, (A23) furconazole, (A24) furconazol-cis, (A25) hexaconazole, (A26) imazalil, (A27) imazalil sulfate (A28) imibenconazole, (A29) ipconazole, (A30) metconazole, (A31) miclobutanil, (A32) naphthifine, (A33) nuarimol, (A34) oxpoconazole, (A35) paclobutrazol, (A36) pefiirazoate, (A37) penconazole (A38) piperalin, (A39) prochloraz, ( A40) propiconazole, (A41) protioconazole, (A42) pyributicarb, (A43) pyrifenox, (A44) quinconazole, (A45) simeconazole, (A46) spiroxamine, (A47) tebuconazole (A48) fine terbine, (A49) tetraconazole, ( A50) triadimefon, (A51) triadimenol, (A52) tridemorph, (A53 ) triflumizole, (A54) triforin, (A55) triticonazole, (A56) uniconazole, (A57) uniconazole-p, (A58) viniconazole, (A59) voriconazole, (A60) l- (4-chlorophenyl) -2- (1H -1, 2,4-triazol-1-yl) cycloheptanol, (A61) methyl 1- (2,2-dimethyl-2,3-dihydro-1H-indeno-1-yl) -1H-imidazole-5carboxylate , (A62) N '- {5- (difluoromethyl) -2-methyl-4- [3- (trimethylsilyl) propoxy] phenyl} -N-ethyl-N-methylimidoformamide, (A63) N-ethyl-N-methyl- N '- {2-methyl-5 (trifluoromethyl) -4- [3- (trimethylsilyl) propoxy] phenyl} imidoformamide, (A64) O [l- (4-methoxyphenoxy) -3,3-dimethylbutan-2-yl] -IH-imidazole-1-carbothioate, (A65) Pyrisoxazole, (A66) 2 - {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4 -dihydro-3H-1,2,4-triazole-3-thione, (A67) 3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} - 1H-1,2,4-triazol-5-yl, (A68) 5- (allylsulfanyl) -l- {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -lH- 1,2,4-triazole, (A69) 2- [1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6trimethyl-heptane-4-yl] -2,4- dihydro-3H-l , 2,4-triazole-3-thione, (A70) 2 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro

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40/154

3H-1,2,4-triazole-3-thione, (A71) 2 - {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4difluorophenyl) oxiran-2-yl] methyl } -2,4-dihydro-3H-1,2,4-triazole-3-thione, (A72)

1- {[king (2R, 3S) -3- (2-chlorophenyl thiocyanate) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole-5 -yl, (A73) 1 - {[rel (2R, 3R)-3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1, 2,4 -triazol-5-yl, (A74) 5- (allylsulfanyl) -l - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole, (A75) 5- (allylsulfanyl) -l - {[rel (2R, 3R) -3 (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran -2-yl] methyl} -1H-1,2,4-triazole, (A76)

2- [(2S, 4S, 5S) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethyl-heptane-4-yl] -2,4dihydro-3H-1, 2,4-triazol-3-thione, (A77) 2 - [(2R, 4S, 5S) -l- (2,4-dichlorophenyl) -5hydroxy-2,6,6-trimethyl-heptane-4-yl ] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (A78) 2 - [(2R, 4R, 5R) -1- (2,4-dichlorophenyl) -5- hydroxy-2,6,6-trimethyl-heptane-4yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione (A79) 2 - [(2S, 4R, 5R) - 1- (2,4dichlorophenyl) -5-hydroxy-2,6,6-trimethyl-heptane-4-yl] -2,4-dihydro-3H- 1,2,4triazole-3-thione, (A80) 2 - [(2S, 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6trimethyl-heptanoo-4-yl] -2,4-dihydro-3H-1, 2,4-triazol-3-thione, (A81) 2 - [(2R, 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy -2,6,6-trimethyl-heptane-4- yl] -2,4-dihydro3H-1,2,4-triazole-3-thione, (A82) 2 - [(2R, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy2 , 6,6-trimethyl-heptane-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (A83) 2- [(2S, 4R, 5S) - 1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethyl-heptane-4-yl] -2,4-dihydro3H-1,2,4-triazole-3-thione, ( A84) 2- [4- (4-chlor ofenoxy) -2- (trifluoromethyl) phenyl] -

1- (1H- 1,2,4-triazol-1-yl) propan-2-ol (A85) 2- [4- (4-chlorophenoxy) -2 (trifluoromethyl) phenyl] -1- (1H- 1, 2,4-triazol-1-yl) butan-2-o 1, (A86) 2- [4- (4chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazole- 1-yl) pentan-2-ol, (A87) 2- [2-chloro-4- (4-chlorophenoxy) phenyl] -1- (1H-1,2,4-triazol-1-yl) butan-2 -ol, (A88) 2- [2-chloro- 4- (2,4-dichlorophenoxy) phenyl] -1- (1H-1,2,4-triazol-1-yl) propan-

2- ol, (A89) (2R) -2- (l-chlorocyclopropyl) -4 - [(lR) -2,2-dichlorocyclopropyl] -1- (1H-

1,2,4-triazol-l-yl) butan-2-ol, (A90) (2R) -2- (l-chlorocyclopropyl) -4 - [(lS) -2,2

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41/154 dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (A91) (2S) -2- (1 chlorocyclopropyl) -4- [(1S) - 2,2-dichlorocyclopropyl] -1 - (1 Η- 1,2,4-triazol-1-yl) butan-2-ol, (A92) (2S) -2- (l-chlorocyclopropyl) -4 - [( 1R) -2,2-dichlorocyclopropyl] -1 (1H-1,2,4-triazol-1-yl) butan-2-ol, (A93) (IS, 2R, 5R) -5- (4-chlorobenzyl) -2 (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (A94) (IR, 2S, 5S) -5 - (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1 - (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (A95) 5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-l- (1H-1, 2,4triazol-1-ylmethyl) cyclopentanol

B) Inhibitors of the respiratory chain in complex I or II, for example (B01) bixafen, (B02) boscalide, (B03) carboxine, (B04) ci-propamide, (B05) diflumetorim, (B06) fenfuram, (B07) fluopiramide , (B08) flutolanil, (B09) fluxpyroxade, (BIO) furametpir, (Bl 1) furmeciclox, (Bl2) isopirazam (mixture of syn-epimeric racemate IRS, 4SR, 9RS and anti-epimeric racemate IRS, 4SR, 9SR), (Bl3 isopirazam (anti-epimetic racemate IRS, 4SR, 9SR), (B14) isopirazam (anti-epimetic enantiomer 1R, 4S, 9S), (B15) isopyrazam (anti-epimetic enantiomer IS, 4R, 9R), isopirazane (Bl6 ) (IRS syn-epimetic racema, 4SR, 9RS), (B17) isopyrazam (1R, 4S, 9R syn-epimeric enantiomer), (B18) isopyrazam (IS-4R, 9S syn-epimeric enantiomer), (B19) mepronil, (B20) oxycarboxine, (B21) penflufen, (B22) pentiopirate, (B23) pyriflumetophen, (B24) silkxane, (B25) tifluzamide, (B26) 1-methyl-N- [2- (1,1,2,2 - tetrafluoroethoxy) phenyl] -3 (trifluoromethyl) -1H-pyrazole-4-carboxamide, (B27) 3- (difluoromethyl) -1-methyl-N [2- (1,1,2,2-tetrafluoroet oxy) phenyl] -1H -pyrazole-4-carboxamide, (B28) 3 (difluoromethyl) -N- [4-fluoro-2- (1,2,2,3,3,3-hexafluoropropoxy) phenyl] -1- methylIH-pyrazole 4-carboxamide, (B29) N- [1- (2,4-dichlorophenyl) -1-methoxypropan-2yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (B30 ) 5,8-difluoroN- [2- (2-fluoro-4 - {[4- (trifluoromethyl) pyridin-2-yl] oxy} -phenyl) ethyl] quinazolin-4amine, (B31) benzovindiflupir, (B32) N - [(1S, 4R) -9- (dichloromethylene) -l, 2,3,4tetrahydro-1,4-methanonaphthalen-5-yl] -3- (difluoromethyl) -l-methyl-1H-pyrazole-4 -

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42/154 carboxamide, (B33) N - [(1R, 4S) -9- (dichloromethylene) -l, 2,3,4-tetrahydro-1,4methanonaphthalen-5-yl] -3- (difluoromethyl) - 1-methyl-1H-pyrazole-4-carboxamide, (B34) 3- (difluoromethyl) -1-methyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-indene-4- yl) -lH-pyrazole-4-carboxamide, (B35) 1,2,5-trimethyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl) -lH- pyrazole 4-carboxamide, (B36) 1-methyl-3 (trifluoromethyl) -N- (1,1,3-trimethyl-2,3-dihydro-1H-indeno-4-yl) -1H-pyrazol-4carboxamide , (B37) 1-methyl-3- (trifluoro ethyl) -N - [(3R) -1,3-trimethyl-2,3-dihydro-1H-indeno-4-yl] -1H-pyrazole-4 -carboxamide, (B38) 1-methyl-3 (trifluoromethyl) -N- [(3S) -1, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1Hpyazole-4 -carboxamide, (B39) 3- (difluoromethyl) -1-methyl-N - [(3S) -1, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole- 4-carboxamide, (B40) 3 (difluoromethyl) -1-methyl-N - [(3R) -1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] 1H-pyrazole -4-carboxamide, (B41) 1,3 5-trimethyl-N - [(3R) -1, 3-trimethyl-2,3-dihydro-1H-indeno-4-yl] -1H-pyrazole -4-carboxamide, (B42) 1,3,5-trimethyl-N [(3S) -1,1,3-trimethyl-2,3-dihydro-1 H-indene-4-yl] -1 H -pyrazol-4-carboxamide, (B43) benodanyl, (B44) 2-chloro-N- (1,3,3-trimethyl-2,3-dihydro-1H-indene-4-yl) pyridine-3- carboxamide, (B45) Isofetamide, (B46) 1-methyl-3- (trifluoromethyl) -N [2 '- (trifluoromethyl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (B47) N- (4 'chlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (B48) N- (2 4'-dichlorobiphenyl-2-yl) -3- (difluoromethyl) -l -methyl-1H-pyrazol-4carboxamide, (B49) 3- (difluoromethyl) -1-methyl-N- [4 '- (trifluoromethyl) biphenyl-2yl] -1H-pyrazole-4-carboxamide, (B50) N- ( 2 ', 5'-difluorobiphenyl-2-yl) -1-methyl-3 (trifluoromethyl) -1H-pyrazole-4-carboxamide, (B51) 3- (difluoromethyl) -1-methyl-N [4' - (prop -l-in-1-yl) biphenyl-2-yl] -lH-pyrazole-4-carboxamide, (B52) 5-fluoro-

1,3-dimethyl-N- [4 '- (prop-l-in -1-yl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (B53) 2-chloro-N- [4' - (prop-1-in-1-yl) biphenyl-2-yl] nicotinamide, (B54) 3 (difluoromethyl) -N- [4 '- (3,3-dimethylbut-l-in-l-yl) biphenyl -2-yl] - 1-methyl-1Hpyazole-4-carboxamide (B55) N- [4 '- (3,3-dimethylbut-l-in-l-yl) biphenyl-2-yl] -5

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43/154 fluoro-1,3-dimethyl-1H-pyrazol-4-carboxamide, (B56) 3- (difluoromethyl) -N- (4'ethynylbiphenyl-2-yl) -l-methyl-1 H-pyrazole-4 -carboxamide, (B57) N- (4'-ethynylbiphenyl-

2- 11) -5-fluoro-1,3-dimethyl-1 H-pyrazole-4-carboxamide, (B 5 8) 2-chloro-N - (4 '- ethinylbiphenyl-2-yl) nicotinamide, (B59) 2-chloro-N- [4 '- (3,3-dimethylbut-l-in-1-yl) biphenyl-2-yl] nicotinamide, (B60) 4- (difluoromethyl) -2-methyl-N- [4 (trifluoromethyl) biphenyl-2-yl] -1, 3-thiazole-5-carboxamide, (B61) 5-fluoro-N- [4 '(3-hydroxy-3-methylbut-l-in-l-yl) biphenyl -2-yl] -1,3-dimethyl-1H-pyrazole-4carboxamide, (B62) 2-chloro-N- [4 '- (3-hydroxy-3-methylbut-l-in-l-yl) biphenyl- 2-yl] nicotinamide, (B63) 3- (difluoromethyl) -N- [4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] -1-methyl-1H - pyrazole-4-carboxamide, (B64) 5-fluoro-N- [4 '- (3methoxy-3-methylbut-1-yn -1-yl) biphenyl-2-yl] -1,3-dimethyl-1H- pyrazole-4carboxamide, (B65) 2-chloro-N- [4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] nicotinamide, (B66) 1,3-dimethyl -N- (1,1,3-trimethyl-2,3-dihydro-1H-indeno-4-yl) 1H -pyrazole-4-carboxamide, (B67) 1,3-dimethyl-N - [(3R ) -1,3,3-trimethyl-2,3-dihydro-1H-indeno-4-yl] -IH-pyrazole-4-carboxamide, (B68) 1,3-d imethyl-N - [(3S) -

1.1.3- trimethyl-2,3-dihydro-1H-indeno-4-yl] -1H-pyrazole-4-carboxamide (B69)

3- (difluoromethyl) -N-methoxy-1-methyl-N- [1- (2,4,6-trichlorophenyl) propan-2-yl] -1H-pyrazol-4-carboxamide, (B70) 3- (difluoromethyl ) -N- (7-fluoro-1,3,3-trimethyl-2,3dihydro-1H-inden-4-yl) -1-methyl-1H-pyrazole-4-carboxamide (B71) 3 (difluoromethyl) -N - [(3, R) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-indeno-4-yl] 1-methyl-1H-pyrazole-4-carboxamide, (B72) 3- (difluoromethyl) -N - [(3S) -7-fluoro-

1.1.3- trimethyl-2,3-dihydro-1 H-indeno-4-yl] 1-methyl-1 H-pyrazole-4-carboxamide.

C) Complex III respiratory chain inhibitors, for example (C01) ametoctradine, (C02) amisulbrom, (C03) azoxystrobin, (C04) cyanofamide, (C05) coumetoxistrobin, (C06) coumoxystrobin, (C07) dimoxystrobin, (C08) enoxastrobin, (C09) famoxadone, (CIO) phenamidone, (Cl 1) phenaminstrobin, (C12) fluphenoxystrobin, (C13) fluoxastrobin, (C14) cresoxim-methyl, (C15) metominostrobin, (C16) mandestrobin, (C17) orysastrobin, (C18)

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44/154 picoxystrobin, (Cl9) pyraclostrobin, (C20) pyrametostrobin, (Cl8) C21) pyranoxystrobin, (C22) pyribencarb, (C23) triclopyrricarb, (C24) trifloxystrobin, (C25) (2E) -2- (2- { [6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidine-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylacetamide, (C26) (2E) -2- (methoxyimino) -N -methyl2- (2 - {[({(1E) -1- [3- (trifluoromethyl) phenyl] ethylidene] amino) oxy] methyl] phenyl) acetamide, (C27) (2E) -2- (methoxyimino) -N -methyl-2- {2 - [(E) - ({l- [3 (trifluoromethyl) phenyl] ethoxy] imino) methyl] phenyl] acetamide, (C28) (2E) -2- {2 [({[( lE) -l- (3 - {[(E) -l-fluoro-2-phenylvinyl] oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N- methylacetamide (C29) Phenaminostrobin , (C30) 5-methoxy-2-methyl-4- (2 - {[({(lE) -l- [3- (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) -2,4- dihydro-3H-1,2,4-triazole-3-one, (C31) methyl (2E) 2- {2 - [({cyclopropyl [(4-methoxyphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3methoxyacrylate, (C32) N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formamide-2h idroxybenzamide, (C33) 2- {2 - ((2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-Nmethylacetamide, (C34) 2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} - 2-methoxy-Nmethylacetamide, (C35) (2E, 3Z) -5 - {[1- (4-chlorophenyl) -1H-pyrazol-3-yl] oxy} -2 (methoxyimino) -N, 3-dimethylpent-3 -enamide.

D) Mitosis and cell division inhibitors, for example (DOI) benomyl, (D02) carbendazim, (D03) chlorphenazole, (D04) dietofencreat, (D05) etabboxam, (D06) fluopicolide, (D07) fiiberidazole, (D08) pencycuron , (D09) thiabendazole, (DIO) methyl thiophanate, (D11) thiophanate, (D12) zoxamide, (D13) 5-chloro-7- (4 methylpiperidin-1-11) -6- (2,4,6-trifluorophenyl ) [1,2,4] triazolo [1,5-a] pyrimidine, (D14) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6- trifluorophenyl) pyridazine.

E) Compounds capable of having an action in several places, for example (E01) mixture of bordeaux, (E02) captafol, (E03) captan, (E04) chlorothalonil, (E05) copper hydroxide, (E06) copper naphthenate, (E07) copper oxide, (E08) copper oxychloride, (E09) copper sulfate (2+), (E10) dichlofluanide, (Ell) dithianone, (E12) dodine, (E13)

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45/154 dodine free base, (E14) ferbam, (E15) fluorofolide, (E16) folpet, (E17) guazatin, (E18) guazatin acetate, (E19) iminoctadine, (E20) iminoctadine albesylate, (E21) triacetin of iminoctadine, (E22) mancopper, (E23) mancozeb, (E24) manebe, (E25) metamorph, (E26) meth zinc, (E27) oxin copper, (E26) E28) propamidine, (E29) propineb, (E30) prepare Sulfur and sulfur bias including calcium polysulphide, (E31) thiram, (E32) tolylfluanide, (E33) zineb, (E34) ziram, (E35) anilazine.

F) Compounds capable of inducing a defense of the host, for example (FOI) acibenzolar-S-methyl, (F02) isothianyl, (F03) probenazole, (F04) thiadinyl, (F05) laminarin.

G) Amino acid and / or protein biosynthesis inhibitors, for example (G01) andoprim, (G02) blasticidin-S, (G03) cyprodinil, (G04) casugamycin, (G05) casugamycin hydrochloride hydrate, (G06) mepanipirim, (G07) pyrimethanil, (G08) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinoline-1-yl) quinoline, (G09) oxytetracycline, (G10) streptomycin. Inhibitors of ATP production, for example (H01) phentin acetate, (H02) fentin chloride, (H03) fentin hydroxide, (H04) siltiofame.

H) Inhibitors of cell wall synthesis, for example (101) bentiavalicarb, (102) dimetomorph, (103) flumorph, (104) iprovalicarb, (105) mandipropamide, (106) polyoxins, (107) polyoxorin, (108) validamycin A, (109) valiphenalate, (110) polyoxin B, (Ill) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -l (morpholin-4-yl) prop 2-en-l-one, (112) (2Z) -3- (4-tert-butylphenyl) -3- (2chloropyridin-4-yl) -l- (morpholin-4-yl) prop-2 -en -canvas.

I) Lipid and membrane synthesis inhibitors, for example (J01) biphenyl, (J02) chloroneb, (J03) dichlorane, (J04) edifenfos, (J05) etridiazole, (J06) iodocarb, (J07) iprobenfos, (J08) isoprothiolane, (J09) propamocarb, (J10) propamocarb hydrochloride, (J11) protiocarb, (J12) pyrazophos, (J13) quintozene, (J14) technazene, (J15) tocophos-methyl.

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46/154

J) Melanin biosynthesis inhibitors, for example (KOI) carpropamide, (K02) diclocimeter, (K03) phenoxanil, (K04) phthalide, (K05) piroquilon, (K06) tolprocarb, (K07) tricyclazole.

K) Nucleic acid synthesis inhibitors, for example (L01) benalaxyl, (L02) benalaxyl-M (kiralaxil), (L03) bupirimate, (L04) clozilacon, (L05) dimethyrimol, (L06) ethirimol, (L07) furalaxil , (L05) L08) himexazole, (L09) metalaxyl, (IOL) metalaxyl-M (mefenoxam), (Lil) ofurace, (LI2) oxadixyl, (LI3) oxolic acid, (L14) octylinone.

L) Signal transduction inhibitors, for example (MOI) clozolinate, (M02) fenpiclonil, (M03) fludioxonil, (M04) iprodione, (M05) procymidone, (M06) quinoxifen, (M07) vinclozoline, (M08) proquinazide.

M) Compounds capable of acting as a decoupler, for example (N01) binapacril, (N02) dinocap, (N03) fermimzon, (N04) fluazinam, (N05) meptildinocap.

N) Other compounds, for example (OOl) bentiazole, (002) betoxazine, (003) capsymicin, (004) carvone, (005) chinomethionate, (006) pyrophenone (clazafenone), (007) cufraneb, (008) ciflufenamide, (009) cymoxanil, (010) cyprosulfamide, (Oil) dazomet, (012) debacarb, (013) dichlorophen, (014) diclobentiazox, (015) diclomezine, (016) difenzoquat, (017) diphenylquate methylsulfate, (018) , (019) ecomate, (020) phenpyrazamine, (021) phenhexamine, (022) flumetover, (023) fluoroimide, (024) flusulfamide, (025) flutianyl, (026) fosetyl aluminum, (027) fosetyl calcium, (028) fosetil-sodium, (029) hexachlorobenzene, (030) irumamycin, (031) isothianyl, (032) metasulfocarb, (033) methyl isothiocyanate, (034) metrafenone, (035) mildiomycin, (036) natamycin, (( 037) nickel dimethyldithiocarbamate, (038) nitrotyl-isopropyl, (039) oxamocarb, (040) oxyphentin, (041) pentachlorophenol and salts, (042) phenothrin, (043) picarbutrazox (044) phosphorous and their salts, (045 ) propamocarb-phylosis tyla (046) propanosine-sodium, (047) pyrimorph, (048)

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47/154 pyraziflumide (049) pyrrolnitrine, (050) tebufloquine, (051) tectophthalam, (052) tolnifanide, (053) triazide, (054) triclamide, (055)) zarylamide, (056) (3S, 6S, 7R, 8R) -8-benzyl-3 - [({3 - [(isobutyryloxy) methoxy] -4-methoxypyridine-2-yl} carbonyl) amino] -6-methyl -4,9-dioxo-1,5-dioxonan- 7-yl 2-methylpropanoate, (057) 1- (4- {4 - [(5R) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl ] -1,3thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (058) 1- (4- {4 - [(5S) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-11 ) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (059) oxatiapproline, (060) 1- (4-methoxyphenoxy) -3,3-dimethylbutan-2-yl -imidazole-1-carboxylate, (061) 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, (062) 2,3-dibutyl-6-chlorothieno [2,3-d] pyrimidin-4 ( 3H) -one, (063) 2,6-dimethyl1H, 5H- [1,4] dithino [2,3-c: 5,6-c '] dipyrrole-1,3,5,7 (2H, 6H) -tetrone, (064) 2 [5-methyl-3- (trifluoromethyl) -lH-pi razol-1-yl] -1- (4- {4 - [(5R) -5-phenyl-4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl } piperidin-1-yl) ethanone, (065) 2- [5methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- (4- {4- 4 - [(5S) -5-phenyl -4,5-dihydro-

1.2- oxazol-3-yl] -1, 3-thiazol-2-yl} piperidin-1-yl) ethanone, (066) 2- [5-methyl-3 (trifluoromethyl) -1H-pyrazol -] - yl] -1- {4- [4- (5-phenyl-4,5-dihydro-1,2-oxazol-3yl) -1,3-thiazol-2-yl] piperidin-1-yl} ethanone, ( 067) 2-butoxy-6-iodo-3-propyl-4Hcromen-4-one, (068) 2-chloro-5- [2-chloro-1- (2,6-difluoro-4-methoxyphenyl) -4- methyl1H-imidazol-5-yl] pyridine, (069) 2-phenylphenol and salts, (070) 3- (4 4,5-trifluoro-

3.3- dimethyl-3,4-dihydroisoquinoline-1-yl) quinoline, (071) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (072) 3-chloro-5- (4-chlorophenyl) - 4- (2,6difluorophenyl) -6-methylpyridazine, (073) 4- (4-chlorophenyl) -5- (2,6-difluorophenyl) 3,6-dimethylpyridazine, (074) 3-chloro-4- (2, 6-difluorophenyl) -6-methyl-5-phenylpyridazine, (075) 5-amino-1,3,4-thiadiazole-2-thiol, (076) 5-ch loro-N'-phenylN '- (prop-2-in -l-yl) thiophene-2-sulfonhydrazide, (077) 5-fluoro-2 - [(4fluorobenzyl) oxy] pyrimidine-4-amine, (078) 5-fluoro-2 - [(4-methylbenzyl) oxy ] pyrimidin-4-amine, (079) 5-methyl-6-octyl [1,2,4] triazolo [1,5-a] pyrimidine-7Petition 870190078277, of 8/13/2019, p. 53/187

48/154 amine, (080) ethyl (2Z) -3-amino-2-cyano-3-phenylacrylate, (081) N '- (4- {[3- (4 chlorobenzyl) -!, 2,4-thiadiazole - 5 -yl] oxy} -2,5-dimethylphenyl) -N-ethyl-Nmethylimidoformamide, (082) N- (4-chlorobenzyl) -3- [3-methoxy-4- (prop-2-ino-1yloxy) phenyl ] propanamide, (083) N - [(4-chlorophenyl) (cyano) methyl] -3- [3-methoxy-

4- (prop-2-in-1-yloxy) phenyl] propanamide, (084) N - [(5-bromo-3-chloropyridine-2yl) methyl] -2,4-dichloronicotinamide, (085) N- [l - (5-bromo-3-chloropyridine-2-yl) ethyl] -2,4-dichloronicotinamide, (086) N- [1- (5-bromo-3-chloropyridine-2-yl) ethyl] -2-fluoro -4-iodonicotinamide, (087) N - {(E) - [(cyclopropylmethoxy) imino] [6 (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-phenylacetamide, (088) N - {(Z) [ (cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2 phenylacetamide, (089) N '- {4 - [(3-tert-butyl-4-cyano-1,2-thiazole -5-yl) oxy] -2-chloro-

5- methylphenyl} -N-ethyl- N-methylimidoformamide, (090) N-methyl-2- (l - {[5-methyl-3 (trifluoromethyl) -1H-pyrazol-l-yl] acetyl} piperidin-4- il) -N- (1,2,3,4-tetrahydronaphthalen-1-11) -1,3-thiazole-4-carboxamide, (091) N-methyl-2- (1 - {[5-methyl-3 (trifluoromethyl) -1H-pyrazol 1-yl] acetyl} piperidin-4-yl) -N - [(1R) -1, 2,3,4-tetrahydronaphthalen-1-yl] -1,3-thiazole-4- carboxamide, (092) N -methyl-2- (1 - {[5-methyl-3 (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -N - [(1S) -l , 2,3,4-tetrahydronaphthalen-1-yl] -1,3-thiazole-4-carboxamide, {093) pentyl {6 - [({[(1-methyl-1Htetrazol-5-yl) (phenyl) methylene ] amino} oxy) methyl] pyridine-2-yl} carbamate, (094) phenazine-1-carboxylic, (095) quinoline-8-ol, (096) quinoline-8-ol sulfate (2: 1), (097 ) tert -6 butyl {6 - [({[(1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridine-2-yl} carbamate, (098) (5- bromo-2-methoxy-4methylpyridine-3-yl) (2,3,4-trimethoxy-6-methylphenyl) methanone, (099) N- [2- (4- {[3 (4-chlorophenyl) prop-2- in-l-yl] oxy] -3-methoxyphenyl) tactile] -N2- ( methylsulfonyl) valinamide, (OlOO) 4-oxo-4 - [(2-phenylethyl) amino] butanoic, (OlOl) but-3-in-lil- {6 - [({[(Z) - (l-methyl- 1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridine 2-yl] carbamate, (0102) 4-amino-5-fluoropyrimidine-2-ol (tautomeric form: 4-amino-5- fluoropyrimidine-2 (IH) -one), 3,4,5-trihydroxybenzoate

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49/154 of (0103) propyl, (0104) [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2oxazol-4-yl] (pyridine-3-yl) methanol, (0105) (S) - [3- (4-chloro-2-fluorophenyl) -5- (2,

4-difluorophenyl) -1,2-oxazol-4-yl] (pyridine-3-yl) methanol, (0106) (R) - [3- (4-chloro-

2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridine-3-yl) methanol, (0107) 2-fluoro-6- (trifluoromethyl) -N- ( 1,3-trimethyl-2,3-dihydro-1H-indene-4yl) -benzamide, (0108) 2- (6-benzylpyridine-2-yl) quinazoline, (0109) 2- [6- ( 3fluoro-4-methoxyphenyl) -5-methylpyridine 2-yl] quinazoline, (0110) 3- (4,4-difluoro-

3,3-dimethyl-3,4-dihydroisoquinoline-1-yl) quinoline, (0111) absetic acid, (0112) N '- [5-bromo-6- (2,3-dihydro-1H- indeno-2-yloxy) -2-methylpyridine-3-yl] N-ethyl-N-methylimidoformamide, (0113) N '- {5-bromo- 6- [l- (3,5-difluorophenyl) ethoxy] -2 -methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (0114) N '- {5bromo-6 - [(1R) -l- (3,5-difluorophenyl) ethoxy] -2-methylpyridine-3- il} -N-ethyl-N-methyl midoformamide, (0115) N '- {5-bromo-6 - [(1S) -l- (3,5-difluorophenyl) ethoxy] -2methylpyridine-3-yl} -N -ethyl-N-methylimidoformamide, (0116) N '- {5-bromo-6 [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridine-3-yl} -N-ethyl-Nmethylimidoformamide, (0117) N '- {5-bromo -6 - [(trans-4-isopropylcyclohexyl) oxy] -2-methylpyridine-3-yl} -N-ethyl-N-methylimidoformamide, (0118) N- cyclopropyl-3- ( difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -l-methyl-1Hpyazole-4-carboxamide, (0119) N-cyclopropyl-N- (2-cyclopropylbenzyl) -3 (difluoromethyl) -5-fluoro-1 -methyl-1H-pyrazole 4-carboxamide, (0120) N- (2-tertbutylbenzyl) -N-cyclopropyl-3 - (dif fluoromethyl) -5-fluoro-1 - methyl-1 H-pyrazole-4carboxamide, (0121) N- (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -

5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (0122) N- (5-chloro-2-isopropylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H - pyrazole-

4-carboxamide, (0123) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5 fluorobenzyl) -5-fluoro-1-methyl-1H-pyrazol-4-carb oxamide, (0124) Ncyclopropyl-3 - (difluoromethyl) -5-fluoro-N- (5-fluoro-2-isopropylbenzyl) -1-methylH-pyrazole-4-carboxamide, (0125) N-cyclopropyl- N- (2-cyclopropyl-5-

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50/154 fluorobenzyl) -3- (difluoromethyl) -5-fluoro-1 - methyl-1 H-pyrazole-4-carboxamide, (0126) N- (2-cyclopentyl-5-fluorobenzyl) -N -cyclopropyl-3 - (difluoromethyl) -5 fluoro-1-methyl-1H-pyrazole-4-carboxamide, (0127) N-cyclopropyl-3 (difluoromethyl) -5-fluoro-N- (2-fluoro-6-ispropylbenzyl) -! - methyl -1H-pyrazole-4carboxamide, (0128) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-methylbenzyl) -

5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (0129) N-cyclopropyl-3 (difluoromethyl) -5-fluoro-N- (2-isopropyl-5-methylbenzyl) -l-methyl-1H- pyrazole-4carboxamide, (0130) N-cyclopropyl-N- (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (0131) N- (2-tert-butyl -5-methylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1Hpyrazole-4-carboxamide, (0132) N- [5-chloro-2- (trifluoromethyl) benzyl ] -Ncyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (0133) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-N- [ 5-methyl-2 (trifluoromethyl) benzyl] -1H-pyrazole-4-carboxamide, (0134) N- [2-chloro-6 (trifluoromethyl) benzyl] -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro- 1-methyl -1Hpyazole-4-carboxamide, (0135) N- [3-chloro-2-fluoro-6- (trifluoromethyl) benzyl] N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H pyrazolo-4-carboxamide, (0136) N-cyclopropyl-3 - (difluoromethyl) -N- (2-ethyl-4,5 - dimethylbenzyl) -5-fluoro-1 methyl-1 H-pyrazole-4- carboxamide, (0137) N-cyclopropyl-3 - (difluoromethyl) -5 fluoro-N- (2-isopropylbenzyl) -! - methyl-1H-pyrazole-4-carbothioamide, (0138) N '(2,5-dimethyl- 4-phenoxyphenyl) -N-ethyl-N-methylimidoformamide, (0139) N '- {4 - [(4,5dichloro-1,3-thiazol-2-yl) oxy] -2,5-dimethylphenyl} -N- ethyl-N-methylimidoformamide, (0140) N- (4-chloro-2,6-difluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1Hpyrazol-5-amine (0141) 9 -fluoro-2,2-dimethyl-5- (quinoline-3-yl) -2,3-di-1,4-benzoxazepine, (0142) 2- {2-fluoro-6 - [(8-fluoro-2 - methylquinoline-3-yl) oxy] phenyl} propan-2-ol, (0143) 2- {2 - [(7,8-difluoro-2-methylquinoline-3-yl) oxy] -6fluorophenyl} propan-2- ol, (0144) 4- (2-chloro-4-fluorophenyl) -N- (2-fluorophenyl) -

1,3-dimethyl-1H-pyrazol-5-amine, (0145) 4- (2-chloro-4-fluorophenyl) -N- (2,6-

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51/154 difluorophenyl)-1,3-dimethyl-1H-pyrazolo-5-amine, (0146) 4- (2-chloro-4 fluorophenyl) -N- (2-chloro-6-fluorophenyl)-1,3-dimethyl -lH-pyrazol-5-amine, (0147)

4- (2-bromo-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5amine, (0148) N- (2-bromo-6-fluorophenyl) -4- (2-chloro-4-fluorophenyl)-1,3-dimethyl1H-pyrazol-5-amine, (0149) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) -l, 3dimethyl-1H-pyrazol-5-amine, (0150) 4- (2-bromo-4-fluorophenyl) -N- (2-bromo-6fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, ( 0151) 4- (2-bromo-4-fluorophenyl) N- (2-chlorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (0152) N- (2-bromophenyl) -4 (2- chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (0153) 4- (2-chloro-4fluorophenyl) -N- (2-chlorophenyl) -1,3-dimethyl-1H- pyrazol-5-amine, (0154) 4- (2bromo-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (015 5) 4- ( 2-bromo-4-fluorophenyl) -N- (2-fluorophenyl) -1,3-dimethyl-1 H-pyrazol-5 amine, (0156) N '- (4- {3 - [(difluoromethyl) sulfanyl] phenoxy } -2,5-dimethylphenyl) -Netyl-N-methylimidoformamide, (0157) N '- (2,5-dimethyl-4- {3 - [(1,2,2,2-tetrafhioroethyl) sulfanyl] phenoxy} phenyl ) -N-ethyl-N-methylimidoformamide, (0158) N '- ( 2,5-dimethyl-4- {3- [(2,2,2-trifluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-Nmethylimidoformamide, (0159) N '- (2,5-dimethyl-4- { 3 - [(2,2,3,3-tetrafluoropropyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (0160) N '- (2,5-dimethyl-

4- {3 - [(pentafluoroethyl) sulfanyl] phenoxy} phenyl) -N- ethyl-N-methylimidoformamide, (0161) N '- (4 - {[3- (difluoromethoxy) phenyl] sulfanyl} -2,5-dimethylphenyl ) -N-ethyl-Nmethylimidoformamide (0162) N '- (2,5-dimethyl-4- {[3- (1,1,2,2-tetrafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N- methylimidoformamide, (0163) N '- (2,5-dimethyl-4 {[3- (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (0164) N'- (2,5-dimethyl-4 - {[3- (2,2,3,3-tetrafluoropropoxy) phenyl] sulfanyl} phenyl) N-ethyl-N-methylimidoformamide, (0165) N '- (2,5-dimethyl -4- {[3- (pentafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidofomiamide, (0166) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-l-yl] -1 - [4- (4- {5- [2- (prop-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl] -1, 3- thiazol-2-yl) piperidin-1-yl] ethanone,

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52/154 (0167) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {5- [2-fluoro-6 (prop-2-in -l-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (0168) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1 [4- (4- {5- [2-chloro-6- (prop-2-in-1-yloxy) phenyl] - 4,5-dihydro-1,2-oxazol-3-yl} -

1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (0169) 2- {3- [2- (l- {[3,5-bis (difluoromethyl) -1H-pyrolazane methanesulfonate- 1-yl] acetyl} piperidin-4-11) -1,3thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} phenyl, (0170) 2- {3- [2- (l - {[3,5-bis (difluoromethyl) -1 H-pyrazol-1-yl] acetyl} -piperidin-4-yl) -1,3 - thiazol-4-yl] -4,

5-dihydro-1,2-oxazol-5-yl} -3-chlorophenyl methanesulfonate, (0171) 2- [3,5bis (difluoromethyl) -1 H-pyrazol-1-yl] -1- [4 - (4 - {(5S) -5- [2- (prop-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -l, 3 -thiazol-2 -yl) piperidin-1-yl] ethanone, (0172) 2- [3,5-bis (difluoromethyl) -1 H-pyrazol-1-yl] -1- [4- (4 - {( 5R) -5- [2- (prop2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazo-3-yl}-1,3-thiazol-2-yl) piperidin -l-yl] ethanone, (0173) 2- [3,5-bis (difluoromethyl) -1 H-pyrazol-1-yl] -1- [4- (4 - {(5S) -5 [2- fluoro -6- (prop -2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol2-yl) piperidin-1-yl] ethanone, (0174) 2- [3,5-bis (difluoromethyl) -1 H-pyrazol-1-yl] 1- [4- (4 - {(5R) -5- [2- fluoro-6- (prop -2-ino-1-yloxy) phenyl] -4,5-dihydro-1,2oxazol-3-yl}-1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (0175) 2- [3,5-bis (difluoromethyl) -IH-pyraz 1-yl] -1- [4- (4 - {(5S) -5- [2-chloro-6- (prop-2-in-l - yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) -piperidin-1-yl] ethanone, h (0176) 2- [3,5-bis (difluoro methyl) -1 H-pyrazol-1-yl] -1- [4- (4 - {(5R) -5- [2-chloro-

6- (prop-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol -3-yl} -1,3-thiazol-2-yl) piperidin-1-yl ] ethanone, (0177) 2 - {(5S) -3- [2- (1 - {[3,5-bis (difluoromethyl methanesulfonate) -! H-pyrazol-1-yl] acetyl} piperidin-4-yl ) -1, 3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} phenyl, (0178) 2 - {(5R) -3- [2- (l- { [3,5-bis (difluoromethyl) IH-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl 3-methanesulfonate] 4,5-dihydro-1,2 oxazol-5-yl} phenyl, (0179) 2 - {(5S) -3- [2- (l - {[3,5-bis (difluoromethyl) -1 H-pyrazol-1-yl] acetyl} piperidin- 4-yl) -1,3-thiazol-4-yl] -4,5-di

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53/154 3-chlorophenyl hydro-1,2-oxazol-5-yl} -methanesulfonate, (0180) 2 - {(5R) -3 [2- (l- {[3,5-bis (difluoromethyl) - 1H-pyrazol-l-yl] acetyl} piperidin-4-yl) -1, thiazol-4-yl 3-methanesulfonate] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenyl , (0S1) (3S, 6S, 7R, 8R) - [(isobutyryloxy) methoxy] -4methoxypicolinamido} -6-methyl-4,9-dioxo-1,5-dioxonan-7-benzyl-3-isobutyrate -ilo.

[0088] As described above, the compound of formula (I), can be mixed with one or more compatible active compounds selected from the class of insecticides / caricides / nematicides. The active ingredients of the insecticide / acaricide / nematicide classes are specified here by their common names that are known and described, for example in The Pesticide Manual 17th Ed., Or can be searched on the Internet (for example, at www.alanwood. net / pesticides).

(1) Acetylcholinesterase (AChE) inhibitors such as carbamates, for example alanocarb, aldicarb, bendiocarb, benfuracarb, butocarboxy, butoxycarboxy, carbaryl, carbofuran, carbosulfan, etiofencarb, phenobucarb, formetanate, methoxycarb, methoxycarb, methoxycarbonate, methoxycarbonate, methoxycarbonate, methoxycarbonate, methoxycarbonate, methoxycarbonate, methoxycarbonate, , pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimetacard, XMC and xylylcarb or organophosphates, such as acephate, azametiphos, azinfos-ethyl, azinfos-methyl, cadusafos, chloretoxifos, chlorfenvinfos, chloroformes, chloriformes, chloriformes, chloriformes, chloriformes, chloriformes, chloriformes, chloriformes ; ) salicylate, isoxathione, malathion, mecarbam, metamidophos, metidation, mevinphos, monocrotophos, naled, etohoate, oxidemeton-methyl, paration, n-methyl paratio, phentoate, phorate, fo salona, fosmida, fosfamidone, phoxim, pirimiphos-methyl, profenofos, propetiphos, protofos, piraclofos, piridaphenthion, quinalphos, sulfotep,

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54/154 tebupirimfos, temephos, terbufos, tetrachlorvinphos, tiometon, triazophos, triclorfon and vamidothion.

(2) GABA-controlled chloride channel antagonists, such as cyclodiene organochlorines, for example, chlordane and endosulfan orphenylpyrazoles (fiproles), for example etiprole and fipronil.

(3) Sodium channel molecules / voltage-dependent sodium channel blockers, such as pyrethroids, for example acrinatrin, alethrin, d-cis-trans-aletüna, d- / ra / zs-alethrin, bifenthrin, bioalethrin, isomer serum cyclopentenyl biorethrin, bioresmethrin, cycloprotrine, cyfluthrin, betacyphlutrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, teta-cypermethrin, zeta- z.s'-isomers], deltamethrin, empentrin [(EZ) -isomers (IR)], sphenvalerate, etofenprox, fenpropatrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halfenprox, imiprotrine, kadetrine, permethrin, momflu, momflu (IR) -rans-isomer), pralethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, teflutrin, tetramethrin, tetramethrin [(IR) -isomers)], tralometrine and transflutrin or DDT or methoxychlor.

(4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), such as neonicotinoids, for example, acetamipride, clothianidin, dinotefuran, imidacloprid, nitenpiram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupiradifurone.

(5) Allosteric modulators of the nicotinic acetylcholine receptor (nAChR), such as spinosyns, for example, spinetoram and spinosad.

(6) Allosteric chloride channel (GluCl) modulators linked to glutamate, such as avermectins / milbemycins, for example, abamectin, emamectin benzoate, lepimectin and milbemectin.

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55/154 (7) Youth hormone mimetics, such as youth hormone analogs, for example, hydroprene, quinoprene and methoprene or phenoxycarb or pyriproxyphene.

(8) Active compounds with unknown or non-specific mechanisms of action, such as alkyl halides, for example, such as methyl bromide and other alkyl or chloropicrin halides or fluorides or borates or generators of emetic tactics or methyl isocyanate.

(9) Cordoronal organ TRPV channel modulators, such as pyridine azomethine derivatives, for example pimetrozine and pyrifluquinazone or flonicamide.

(10) Mite growth inhibitors, for example clofentezine, hexythiazox and diflorrazine or ethoxazole.

(11) Insect mesenteric gut microbial disruptors, by QXQmploBacillus thuringiensis subspecies israelensis, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and CryillA, Cry2Ab, Vip3a, mCry3A, Cry3Ab, Cry3Bb, Cry34Abl / Cry35Abl.

(12) Inhibitors of mitochondrial ATP synthase such as organotinic miticides, for example, azocyclotine, cyhexatin and fenbutatin oxide or diafentiuron or propargite or tetradifon.

(13) Decouplers of oxidative phosphorylation acting by disrupting the proton gradient, for example, chlorfenapyr, DNOC and sulfluramide.

(14) Nicotinic acetylcholine receptor (nAChR) channel blockers, such as bensultap, cartap-hydrochloride, tiocyclam and thiosultap-sodium.

(15) Chitin biosynthesis inhibitors, type 0, such as bistrifluoron, chlorfluazuron, diflubenzuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

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56/154 (16) Chitin biosynthesis inhibitors, type 1, such as buprofezin.

(17) Seedling disruptors (particularly in Dipteran), such as cyromazine.

(18) Ecdysone receptor agonists, such as chromophenozide, halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists, such as amitraz.

(20) Inhibitors of electron transport of the mitochondrial III complex, such as hydramethylnon or acequinocil or fluacrypyrim or biphenazate.

(21) Electron transport inhibitors of the mitochondrial I complex, for example, METI acaricides and insecticides, for example phenazaquin, fenpyroximate, pyrimidifene, pyridabene, tebufenpirad and tolfenpirad or rotenone (Derris).

(22) Voltage-dependent sodium channel blockers, such as indoxacarb or metaflumizone.

(23) Acetyl-CoA-carboxylase inhibitors, such as derivatives of tetronic and tetramic acid, for example, spirodiclofen, spiromesifene and spirotetramat.

(24) Inhibitors of electron transport of the mitochondrial IV complex, such as phosphides, for example, aluminum phosphide, calcium phosphide, zinc phosphide and phosphine or cyanides.

(25) Mitochondrial II electron transport inhibitors such as beta-ketonitrile derivatives, for example, cyenopyrafen and cyflumetofen or carboxanilides.

(28) Modules of the ryanodine receptor, such as diamides, for example, chlorantraniliprole, cyantraniliprole and flubendiamide.

(29) Cord organ modulators in an undefined target location, such as flonicamide.

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Other active ingredients with unknown or indeterminate mode of action, such as afidopiropen, afoxolaner, azadiractin, benclothiaz, benzoxime, biphenazate, broflanilide, bromopropylate, chinomethionat, cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide, fluoridizone, fluoridizone , flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, lotilaner, meperfluthrin, paichongding, pyflubumide, pyridalyl, pyrifluquinazon, pyriminostrobin, sarolaner, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tioxazafen, triflumezopyrim and iodomethane; in addition, preparations based on Bacillus firmus (1-1582, BioNeem, Votivo) and the following known active compounds: 1- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} -3- (trifluoromethyl) -1H-1,2,4-triazole-5-amine (known from W02006043635), {1 '- [(2E) -3- (4-chlorophenyl) prop-2-eno- l-yl] -5-fluorospiro [indole-3,4'-piperidine] -1 (2H) -yl} (2-chloropyridin-4-yl) methanone (known from W02003106457), 2-chloro-N- [ 2- {l - [(2E) -3- (4-chlorophenyl) prop2-en-1-yl] piperidin-4-yl} -4- (trifluoromethyl) phenyl] isonicotinamide (known from document W02006003494), 3- ( 2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1,8diazaspiro [4.5] dec-3-en-2-one (known from W02009049851), 3- (2,5-dimethylphenyl) ethyl carbonate -8- methoxy-2-oxo-1,8,8-diazospiro [4.5] dec-3-en-4-yl (known from W02009049851), 4- (but-2-in-1-yloxy) -6- ( 3,5 - dimethylpiperidin-1-yl) -5 fluoropyrimidine (known from document W02004099160), 4- (but-2-in -1yloxy) -6- (3-chlorophyll nil) pyrimidine (known from document W02003076415), PF1364 (No. CAS- Reg.No. 1204776-60-2), methyl-2- [2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5-chloro-3- methylbenzoyl] -2methylhydrazicarboxylate (known from document W02005085216), methyl-2 [2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5

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58/154 cyano-3-methylbenzoyl] -2-ethylhydrazicarboxylate (known from document W02005085216), methyl-2- [2 - ({[3-bromo-l- (3-chloro-pyridin-2-yl) - 1H -pyrazol-5yl] carbonyl} amino) -5-cyano-3-methylbenzoyl] -2-methyl-hydrazicarboxylate (known from document W02005085216), methyl-2- [3,5-dibromo-2 - ({[3bromo- 1- (3-Chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) benzoyl] -2ethylhydrazicarboxylate (known from document W02005085216), N- [2- (5 amino-1, 3,4 -thiadiazol-2-yl) -4-chloro-6-methylphenyl] -3-bromo-1- (3-chloropyridin-2yl) -1 H-pyrazole-5-carboxamide (known from CN102057925), 4- [5- (3,5dichlorophenyl) -5 - (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2-methyl-N - (1oxidotietan-3-yl) benzamide (known from document W02009080250), N - [(2E) -l - [(6-chloropyridine-3-yl) methyl] pyridin-2 (IH) -yl dene] -2,2,2trifluoroacetamide (known from WO2012029672), l- [ (2-chloro-1,3-thiazol-5-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidine-li-2-olate (known from W02009099929), 1 - [ (6-chloropyridin-3-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2 a] pyrimidin-1-ium-2-olate (known from W02009099929), 4- (3 { 2,6-dichloro-4 - [(3,3-dichloroprop-2-en-1-yl) oxy] phenoxy] propoxy) -2-methoxy-6 (trifluoromethyl) pyrimidine (known from CN101337940), N- [2- (tertbutylcarbamoyl) -4-chloro-6-methylphenyl] -1- (3-chloropyridin-2-yl) -3- (fluoromethoxy) 1H-pyrazole-5-carboxamide (known from document W02008134969), butyl [2 - (2,4-dichlorophenyl) -3-oxo-4-oxaspiro [4.5] dec-l-en -1-yl] carbonate (disclosed in CN102060818), 3 (E) -3- [l - [(6 -chloro-3-pyridyl) methyl] -2-pyridyliden]-1,1-trifluoropropan-2- um (known from WO2013144213), N (methylsulfonyl) -6- [2- (pyridin-3-yl) - 1,3-thiazol-5-yl] pyridine-2-carboxamide (known from W02012000896), N- [3- (benzylcarbamoyl) -4-chlorophenyl] -1methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -lH - pyrazole-5-c arboxamide (known from document W02010051926).

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59/154 [0089] The compounds of formula (I), can be used to treat various fungal pathogens. Non-limiting examples of fungal disease pathogens that can be treated according to the invention include:

Diseases caused by powdery mildew pathogens, for example, Blumeria species, such as Blumeria graminis; Podosphaera species, for example, Podosphaera leucotricha; Sphaerotheca species, for example, Sphaerotheca fuliginea; species of Uncinula, for example, Uncinula necator; Erysiphe species, for example, Erysiphe cichoracearu;

Diseases caused by pathogens of rust disease, for example, by species of Gymnosporangium, for example, Gymnosporangium sabinae; Hemileia species, for example, Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example, Puccinia recondita, Puccinia graminis or Puccinia striiformis; Uromyces species, for example, Uromyces appendiculatus;

Diseases caused by pathogens in the Oomycetes group, for example, Albugo species, for example, Albugo Candida; Bremia species, for example, Bremia lactucae; Peronospora species, for example, Peronospora pisi or P. brassicae; Phytophthora species, for example, Phytophthora infestans; Plasmopara species, for example, Plasmopara viticola; species of Pseudoperonospora, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example, Pythium ultimum;

Leaf spot diseases and diseases caused, for example, by species of Alternaria, for example, Alternaria solani; species of Cercospora, for example, Cercospora beticola; Cladiosporium species, for example, Cladiosporium cucumerinum; Cochliobolus species, for example, Cochliobolus sativus (form of conidia: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, for example,

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Colletotrichum lindemuthanium ', Cycloconium species, for example, Cicloconium oleaginum', Diaporthe species, for example, Diaporthe citrv, Elsinoe species, for example, Elsinoe fawcettii ', Gloeosporium species, for example, Gloeosporium laeticolor, Glomerella species, for example, Glomerella cingulata ', Guignardia species, for example, Guignardia bidwelli', Leptosphaeria species, for example, Leptosphaeria maculans'. Magnaporthe species, for example, Magnaporthe grisea; Microdochium species, for example, Microdochium nivale ', Mycosphaerella species, for example, Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis', Phaeosphaeria species, for example, Phaeosphaeria nodorum; Pyrenophora species, for example, Pyrenophora teres or Pyrenophora tritici rep ends', Ramularia species, for example, Ramularia collo-cygni or Ramularia areola ', Rhynchosporium species, for example, Rhynchosporium secalis', Septoria species, for example, Septoria apii or Septoria lycopersici ', Stagonospora species, for example, Stagonospora nodorum', Typhula species, for example, Typhula incarnata ', Venturia species, for example, Venturia inaequalis', Root and stem diseases caused, for example , by Corticium species, for example, Corticium graminearum ', Fusarium species, for example, Fusarium oxysporum', Gaeumannomyces species, for example, Gaeumannomyces graminis ', Plasmodiophora species, for example, Plasmodiophora brassicae', Rhizoctonia species, for example, Rhizoctonia solani ', Sarocladium species, for example, Sarocladium oryzac, Sclerotium species, for example, Sclerotium oryzae', Tapesia species, for example, Tapesia acuformis ', Thielaviopsis species, for example, Thielaviopsis basicola', Ganoderma species, for example, Gano derma lucidunr,

Ear and panicle diseases (including corn cobs) caused, for example, by Alternaria species, for example, Alternaria spp. ', Species of

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Aspergillus, for example, Aspergillus flavus ', Cladosporium species, for example, Cladosporium cladosporioides', Claviceps species, for example, Claviceps purpurea ', Fusarium species, for example, Fusarium culmorum', Gibber ella species, for example, Gibber ella zeae ', Monographella species, for example, Monographella nivalis', Stagnospora species, for example, Stagnospora nodorum',

Diseases caused by dirt fungi, for example, Sphacelotheca species, for example, Sphacelotheca reiliana ', Tilletia species, for example, Tilletia caries or Tilletia controversa', Urocystis species, for example, Urocystis occulta ', Ustilago species, for example, Ustilago nuda ', Fruit rot caused, for example, by Aspergillus species, for example, Aspergillus flavus', Botrytis species, for example, Botrytis cinerea', Penicillium species, for example, Penicillium expansum or Penicillium purpurogenum ', Rhizopus species, for example, Rhizopus stolonifer, Sclerotinia species, for example, Sclerotinia sclerotiorunr, Verticilium species, for example, Verticilium alboatrum',

Rot and wilt diseases caused by seeds and soil, and also by seedling diseases, caused, for example, by Alternaria species, for example, Alternaria brassicicokr, Aphanomyces species, for example, Aphanomyces euteiches', Ascochyta species, for example, Ascochyta lentis', Aspergillus species, for example, Aspergillus flavus', Cladosporium species, for example, Cladosporium herbarum ', Cochliobolus species, for example, Cochliobolus sativus (conidia form: Drechslera, Bipolaris Syn: Helminththyn ; Colletotrichum species, for example, Colletotrichum coccodes ', Fusarium species, for example, Fusarium culmorum', Gibberella species, for example, Gibberella zeae ', Macrophomina species, for example, Macrophomina phaseolina', Microdochium species, for example , Microdochium nivale ', species of

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Monographella, for example, Monographella nivalis ', Penicillium species, for example, Penicillium expansion', Phoma species, for example, Phoma lingam ', Phomopsis species, for example, Phomopsis soye', Phytophthora species, for example, Phytophthora caclorunr, Pyrenophora species, for example, Pyrenophora graminea ', Pyricularia species, for example, Pyricularia oryzae', Pythium species, for example, Pythium ultimum ', Rhizoctonia species, for example, Rhizoctonia solani', Rhizopus species, for example, Rhizopus oryzae ', Sclerotium species, for example, Sclerotium rolfsii', Septoria species, for example, Septoria nodorunr, Typhula species, for example, Typhula incarnata ', Verticillium species, for example, Verticillium dahliae',

Cancers, galls and witches' broom caused, for example, by species of Nectria, for example, Nectria galligena ', wilt diseases caused, for example, by species of Monilinia, for example, Monilinia laxa',

Deformations of leaves, flowers and fruits, caused, for example, by Exobasidium species, for example, Exobasidium vexans ', Taphrina species, for example, Taphrina deformans',

Degenerative diseases in woody plants, caused, for example, by species of Esca, for example, Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterrânea ', Ganoderma species, for example, Ganoderma boninense',

Diseases of flowers and seeds caused, for example, by species of Botrytis, for example, Botrytis cinerea ', diseases of plant tubers caused, for example, by Rhizoctonia species, for example, Rhizoctonia solani', species of Helminthosporium, for example , Helminthosporium solani ',

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Diseases caused by bacterial pathogens, for example, by Xanthomonas species, for example, Xanthomonas campestris pv. oryz.ae: Pseudomonas species, for example, Pseudomonas syringae pv. lachrymans', species of Erwinia, for example, Erwinia amylovora ', species of Ralstonia, for example, Ralstonia solanacearum',

Fungal diseases in roots and stem base caused, caused, for example, by black root rot (Calonectria crolalariae), coal rot (Macrophomina phaseolind), fusarium rust or wilt, root rot and colon rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), root rot of mycoleptodiscus (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora vasinfecta), rot and stem rust (Diaporthe phaseolorum), stem cancer (Diaporthe phaseolorum var. ca. Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimam), rhizoctonia root rot, decay of the stem and decay of the stem and damping stalk sclerotinia (Sclerotinia sclerotiorum), southern sclerotinia rust (Sclerotinia rolfsii), rot of thielaviopsis roots (Thielaviopsis basicola).

[0090] Plants that can be treated according to the invention include the following: Rosaceae sp (for example, apples, pears, apricots, cherries, peaches and almonds), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp. ., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example, banana trees and plantations), Rubiaceae sp. (e.g., coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example, lemons, oranges and grapefruits); Vitaceae sp. (for example, grapes); Solanaceae sp. (for example, tomatoes, peppers), Eiliaceae sp., Asteraceae sp.

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64/154 (e.g., lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (e.g., cucumber), Alliaceae sp. (for example, leeks, onions), Papilionaceae sp. (for example, peas); main cultivated plants, such as Poaceae / Gramineae sp. (for example, corn, turf, cereals such as wheat, centerio, rice, barley, oats, corn and triticale), Asteraceae sp. (e.g., sunflower), Brassicaceae sp. (for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes and canola, mustard, horseradish and watercress), Fabacae sp. (for example, beans, peanuts), Papilionaceae sp. (for example, soybeans), Solanaceae sp. (for example, potatoes), Chenopodiaceae sp. (eg sugar beet sugar, fodder beet, swiss chard, beet); Malvaceae (for example, cotton); useful and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.

[0091] All plants and parts of the plant can be treated according to the invention. Plants are understood here to mean all plants and plant populations, such as desired and undesirable wild plants or crop plants (including naturally occurring crop plants). Harvesting plants can be plants that can be obtained by conventional optimization and breeding methods or by genetic engineering and biotechnology methods or combinations of these methods, including transgenic plants and including plant crops that are protected and not protected by copyright. plant breeders. Parts of the plant are understood as all the parts and organs of plants above and below the ground, such as the aerial part, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruits, fruits and seeds, roots , tubers and rhizomes. Plant parts also include material harvested and material for vegetative and generative propagation, for example, cuttings, tubers, rhizomes, wedges and seeds.

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The invention also includes a method for seed treatment, especially seeds (dormant, leaf-to-leaf harvest, pre-germinated or even with emerged roots and leaves) treated with at least one of the compounds of the formula (I) and compositions thereof. The seeds of the invention are used in methods for protecting seeds and seedlings emerging from the seeds of harmful phytopathogenic fungi. In these methods, seeds treated with at least one active ingredient of the invention are used.

[0093] It is also desirable to optimize the amount of active ingredient used in order to provide the best possible protection to germinate seeds, plant seedlings and plants emerging from the attack by phytopathogenic fungi, but without damaging the plants with the active ingredient used . In particular, seed treatment methods must also take into account the intrinsic phenotypes of transgenic plants to achieve optimum protection of the seed and plant germination with a minimum of crop protection compositions.

[0094] The present invention, therefore, also relates to a method for protecting seeds, plant germination and emerged seedlings from attacks by animal parasites and / or harmful phytopathogenic microorganisms by treating the seeds with a composition of the invention. The invention also relates to the use of compositions according to the invention for seed treatment to protect seeds, the germination of plants and seedlings emerging against animal parasites and / or phytopathogenic microorganisms. The invention also relates to other seeds that have been treated with a composition of the invention for protection from animal pests and / or phytopathogenic microorganisms.

[0095] One of the advantages of the present invention is that the treatment of seeds with these compositions not only protects the seed itself, but also the plants resulting after emergence, from animal pests and / or

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66/154 harmful phytopathogenic microorganisms. In this way, the immediate treatment of the crop at the time of sowing, or shortly thereafter, protects the plants, as well as the treatment of seeds before sowing. It is also considered advantageous that the active ingredients of the invention or derived compositions can be used mainly also for the transgenic seed, in which case the plant that grows from this seed will be able to express a protein that acts against pests, herbicide damage or stress abiotic. The treatment of such seeds with the active ingredients of the invention or their compositions, for example, an insecticidal protein, can result in control of certain pests. Surprisingly, another synergistic effect can be observed in this case, which in addition increases the effectiveness of protection against the attack of pests, microorganisms, weeds or abiotic stress.

[0096] The compounds of the formula (I) are suitable for protecting seeds of any variety of plants that are used in agriculture, greenhouse, forests or horticulture. More particularly, this occurs with cereal seeds (such as wheat, barley, rye, corn and oats), rapeseed, maize, cotton, soybeans, rice, potatoes, coffee, beans, sunflowers, beets (for example, beet sugar and beets forage), peanuts, vegetables (such as tomatoes, cucumbers, onions and lettuce), lawns and ornamental plants. Of particular importance is the treatment of wheat, soy, rapeseed, corn and rice seeds.

[0097] As also described below, the treatment of transgenic seeds with the active ingredients of the invention or their compositions is of particular significance. This refers to plant seeds that contain at least one heterologous gene that allows expression of a polypeptide or protein, for example, having insecticidal properties. These heterologous genes in transgenic seeds may originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. These heterologous genes originate

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67/154 preferably from Bacillus sp., In which case the genetic product is effective against the European corn borer and / or the western corn rootworm. In particular, the heterologous genes originate, preferably, from Bacillus thuringiensis.

[0098] In the context of the present invention, the composition of the invention is applied to the seeds either alone or in a suitable formulation. Preferably, the seed is treated in a state where it is sufficiently stable so that no damage occurs in the course of treatment. In general, seeds can be treated at any time between harvest and some time after sowing. It is common to use seeds that have been separated from the plant and released from ears of corn, husks, stems, coatings, hair or fruit pulp. For example, it is possible to use seeds that have been harvested, cleaned and dried to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seeds that, after drying, for example, have been treated with water and then dried again, or seeds immediately after leaf to leaf harvest, or seeds stored under leaf to leaf harvest conditions. leaf or pre-germinated, or seeds sown in nursery trays, tapes or paper.

[0099] When treating seeds, in general, it is necessary to ensure that the amount of the composition of the invention applied to the seeds and / or the amount of new food additives is selected in such a way that the germination of the seed is not compromised, or that the resulting plant is not damaged. This should be ensured mainly in the case of active ingredients that can have phytotoxic effects in certain proportions of application.

[0100] The compounds of formula (I) can be applied directly, that is, without containing any other components and without having been diluted. In general, it is preferable to apply the compositions to the seed in the form of

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68/154 of an appropriate formulation. Formulations and methods suitable for seed treatment are known to all those who are qualified to do so. The compounds of formula (I) can be converted to the usual relevant formulations for applications on seeds, such as solutions, emulsions, suspensions, powders, foams, sludges or combined with other seed coating compositions, such as film-forming materials , granulation materials, fine iron or other metallic powders, granules, coating material for inactivated seeds and also ULV formulations. In seed treatment to facilitate plantability, the seeds can be coated with polymer. The polymer coating consists of a binder, a wax and a pigment and one or more stabilizers in an amount effective to stabilize the suspension. The binder can be a polymer selected from the group consisting of vinyl acetylene copolymer, vinyl acetate homopolymer, vinyl-acetate acrylic copolymer, vinyl acrylic, acrylic, ethylene vinyl chloride, vinyl ether maleic anhydride or butadiene styrene. Other polymers can be used.

These formulations are prepared in a known way, mixing the active ingredients, or combinations of active ingredients, with usual additives, such as, for example, usual extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, thickeners secondary, adhesives, gibberellins, and also water. Useful dyes that may be present in seed formulations usable in accordance with the invention are all pigments that are customary for such purposes. It is possible to use pigments, which are partially soluble in water, or dyes, which are soluble in water. Examples include dyes known by the names of Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1.

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69/154 [0101] Useful wetting agents that may be present in seed formulations usable in accordance with the invention are all substances that promote moisture and are conventionally used for the formulation of active agrochemical ingredients. Preferably usable are alkylnaphthalenesulfonates, such as diisopropyl- or diisobutylnaphthalenesulfonates.

[0102] Useful dispersants and / or emulsifiers that may be present in seed formulations usable in accordance with the invention are all non-ionic, ionic and anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Useful non-ionic dispersants especially include ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and trictrylphenol polyglycol ether and their phosphate or sulfate derivatives. Suitable anionic dispersants are especially lignosulfonates, polyacrylic acid salts and arylsulfonate / formaldehyde condensates.

[0103] The defoaming agents that may be present in the seed coating formulations usable according to the invention are all foam inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone defoamers and magnesium stearate can be used preferably.

[0104] The preservatives that can be present in seed coating formulations usable according to the invention are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophene and hemiformal benzyl alcohol.

[0105] Secondary thickeners that may be present in the seed coating formulations usable according to the invention are all

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70/154 substances usable for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, derivatives of acrylic acid, xanthan, modified clays and finely divided silica.

[0106] The adhesives that may be present in seed coating formulations, usable according to the invention, are all the usual binders usable in seed treatment products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

[0107] The formulations for seed applications usable according to the invention can be used to treat a wide variety of different types of seeds, either directly or after previous dilution with water. For example, concentrates or preparations that can be obtained by diluting with water can be used to coat cereal seeds, such as wheat, barley, rye, oats and triticale, as well as corn, soy, rice, rapeseed, peas. , beans, cotton, sunflower and beet, or a wide variety of different vegetable seeds. Formulations usable in accordance with the invention, or diluted preparations thereof, can also be used for seeds of transgenic plants. In this case, additional synergistic effects may also occur in interaction with the substances formed by expression.

[0108] For the treatment of seeds with formulations usable in accordance with the invention, or with the preparations obtained therefrom by the addition of water, all mixing units usually usable for seed applications are useful. Specifically, the procedure in applications on seeds is to put the seeds in a mixer, to add the desired amount of formulations, or after previous dilution with water and mix everything until all the applied formulations are distributed

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71/154 homogeneously on the seeds. If applicable, this is followed by a drying operation.

[0109] The application rate of formulations usable in accordance with the invention can be varied within a relatively wide range. It is guided by the specific content of the active ingredients in the formulations and by the seeds. Application rates for each active ingredient are generally between 0.001 and 15 g of seeds per kilogram, preferably between 5 and 0.01 g / kg of seed.

[0110] When using the compounds of formula (I) as fungicides, application rates can vary within a relatively wide range, depending on the type of application. The application rate of the active ingredients of the invention is:

[0111] In the case of treatment of parts of the plant, for example, leaves: from 0.1 to 10,000 g / ha, preferably from 10 to 1000 g / ha, even more preferably from 30 to 300 g / ha (in the case application by watering or dripping, it is still possible to reduce the application rate, especially when inert substrates, such as rock wool or perlite) are used;

[0112] In the case of seed treatment: from 0.1 to 200 g per 100 kg of seeds, preferably from 1 to 150 g per 100 kg of seeds, preferably from 2.5 to 25 g per 100 kg of seeds , and even more preferably from 2.5 to 12.5 g per 100 kg of seeds;

[0113] In the case of soil treatment: from 0.1 to 10,000 g / ha, preferably from 1 to 5000 g / ha.

[0114] These prices are for example only and not to limit the effects of the invention.

[0115] In some cases, the compounds of formula (I) may, at certain concentrations or rates of application, also be used as herbicides, phytoprotectants, growth regulators or agents to improve

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72/154 properties of plants, or as microbicides such as, for example, fungicides, bactericides, antimycotic viricides (including compositions against viroids) or as compositions against MLO (organisms similar to mycoplasma) and RLO (organisms similar to Rickettsia).

[0116] The compounds of formula (I) are involved in the physiological processes of plants and, therefore, can also be used as growth regulators. Growth regulators can have a variety of effects on plants. The effect of the substances depends essentially on the time of application in relation to the stage of development of the plant, the plant variety and also on the amounts of active ingredient applied to plants and their environment and the type of application. In each case, the growth regulators must have a certain desired effect on the crop plants.

[0117] The growth-regulating effects include earlier germination, better emergence, more developed root system and / or improved root growth, greater tillering capacity, more productive tillers, earlier flowering, increased plant height and / or biomass , shortening of the stems, improvements in sprout growth, number of grains / ears, number of ears / m ² , number of stolons and / or number of flowers, improved harvest index, larger leaves, less dead basal leaves, improved phyllotaxis, earlier fruit ripening / finishing, homogeneous ripening, increased grain filling duration, better fruit finishing, larger fruit / vegetable size, resistance to germination and reduced lodging.

[0118] The increase or improvement refers to the total biomass yield per hectare, yield per hectare, fruit / seed weight, seed size and / or weight per hectolitre, as well as an improvement in product quality, which includes:

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73/154 better processability related to size distribution (seed, fruit, etc.), homogeneous ripening, grain moisture, better grinding, better vinification, better fermentation, higher juice yield, harvest yield, digestibility, sedimentation value, number of falls, pod stability, storage stability, improved fiber length / strength / uniformity, increased milk and / or compliance with the quality of animals fed with silage, adaptation to cooking and frying;

it also comprises an improved marketability with regard to the quality of the grains / fruit, the size distribution (core, fruit, etc.), increased shelf life / storage, firmness / softness, flavor (aroma, texture, etc. .), quality (size, shape, number of berries, etc.), number of berries / fruits per bunch, texture, freshness, covering with wax, frequency of physiological disorders, color, etc .;

further comprising an increase in desired ingredients, such as, for example, proteins, fatty acids, oil content, oil quality, amino acid composition, sugars, acidity (pH), sugar / acid ratio (Brix), polyphenols, content starch, nutritional quality, gluten content / index, energy content, taste, etc .;

and also including a decrease in undesired ingredients, such as, for example, less mycotoxins, less aflatoxins, geosmin level, phenolic flavors, absorption, polyphenols oxidases and peroxidases, nitrate content, etc.

[0119] Plant growth regulating compounds, for example, can be used to slow the vegetative growth of plants. Such growth depression is of economic interest, for example, in the case of grasses, since it is possible to reduce the frequency of grass cutting in ornamental gardens, parks and sports facilities, on roads, airports or in fruit plantations. It is also important to inhibit the growth of herbaceous plants and

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74/154 woody roads and near pipelines or overhead cables, or generally in areas where vigorous plant growth is unwanted. [0120] It is also important to use growth regulators to inhibit the longitudinal growth of cereals. This reduces or completely eliminates the risk of lodging the plants before harvest. In addition, growth regulators, in the case of cereals, can strengthen the stalk, which also prevents lodging. The use of growth regulators to shorten and strengthen stems allows the implantation of larger volumes of fertilizers to increase yield, without any risk of lodging the cereal crop.

[0121] In many cultivated plants, the depression of vegetative growth allows for denser planting and, thus, it is possible to obtain higher yields based on the surface of the soil. Another advantage of smaller plants obtained in this way is that the crop is easier to cultivate and harvest.

[0122] Reducing the vegetative growth of plants can also lead to increased or improved yields, because nutrients and assimilates are more beneficial for the formation of flowers and fruits than for the vegetative parts of plants.

[0123] Alternatively, growth regulators can also be used to promote vegetative growth. This is of great benefit when harvesting the vegetative parts of the plants. However, promoting vegetative growth can also promote generative growth as more assimilates are formed, resulting in more or larger fruits.

[0124] In addition, beneficial effects on growth or yield can be achieved by improving the efficiency of the use of nutrients, especially the efficiency of nitrogen use (N), efficiency of use

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75/154 phosphorus (P), water use efficiency, improved sweating, breathing and / or CO2 nodulation assimilation rate, better Ca metabolism, etc. [0125] Similarly, growth regulators can be used to change the composition of plants, which, in turn, can result in an improvement in the quality of harvested products. Under the influence of growth regulators, parthenocarpic fruits can be formed. In addition, it is possible to influence the sex of the flowers. It is also possible to produce sterile pollen, which is of great importance in the creation and production of hybrid seeds.

[0126] Use of growth regulators can control the branching of plants. On the one hand, by breaking apical dominance, it is possible to promote the development of lateral shoots, which can be highly desirable, especially in the cultivation of ornamental plants, also in combination with a growth inhibition. However, on the other hand, it is also possible to inhibit the growth of lateral shoots. This effect is of particular interest, for example, in growing tobacco or growing tomatoes.

[0127] Under the influence of growth regulators, the amount of leaves on the plants can be controlled in such a way that the defoliation of the plants is achieved in a desired time. Such defoliation plays an important role in mechanized cotton harvesting, but it is also of interest to facilitate harvesting in other crops, for example, viticulture. Defoliation of plants can also be performed to decrease plant transpiration before being transplanted.

[0128] In addition, growth regulators can modulate plant senescence, which can result in a prolonged duration of the green leaf area, in a longer phase of grain filling, improving quality, productivity, etc.

[0129] Growth regulators can also be used to regulate fruit dehiscence. On the one hand, it is possible to avoid dehiscence

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76/154 premature fruit. On the other hand, it is also possible to promote dehiscence of the fruits or even the abortion of flowers to reach a desired mass (thinning). In addition, it is possible to use growth regulators at the time of harvest to reduce the force required to remove the fruit, to allow mechanical harvesting or to facilitate manual harvesting.

[0130] Growth regulators can also be used to achieve faster or delayed ripening of material harvested before or after harvest. This is particularly advantageous as it allows the ideal adjustment to the requirements of the market. In addition, growth regulators, in some cases, can improve the color of the fruit. In addition, growth regulators can also be used to synchronize maturation within a certain period of time. This establishes the prerequisites for complete mechanical or manual harvesting in a single operation, for example, in the case of tobacco, tomatoes or coffee.

[0131] Using growth regulators, it is additionally possible to influence the rest of plant seeds or sprouts, such that plants such as pineapples or ornamental plants in nurseries, for example, germinate, sprout or flower when they would not normally be inclined to do it. In areas where there is a risk of frost, it may be desirable to delay the sprouting or germination of seeds, with the help of growth regulators, in order to avoid damage resulting from late frosts.

[0132] Finally, growth regulators can induce plant resistance to frost, drought or high soil salinity. This allows for the cultivation of plants in regions that would normally be unsuitable for this purpose.

[0133] The compounds of formula (I) also have a potent reinforcing effect on plants. Thus, they can be used to mobilize the plant's defenses against the attack of undesirable microorganisms.

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77/154 [0134] Substances that strengthen plants (resistance inducers), in the present context, are substances capable of stimulating the defense system of plants, in such a way that the treated plants, when subsequently inoculated with undesirable microorganisms, develop a high degree of resistance to these microorganisms.

[0135] In addition, in context with the present invention, plant physiology includes the following effects:

[0136] Abiotic stress tolerance, comprising tolerance to high or low temperatures, drought tolerance and recovery after water stress, water use efficiency (correlating with reduced water consumption), flood tolerance, ozone stress and UV tolerance, tolerance to chemicals like heavy metals, salts and pesticides etc.

[0137] Tolerance to biotic stress with greater resistance to fungi and increased resistance against nematodes, viruses and bacteria. In the context of the present invention, tolerance to biotic stress preferably comprises greater resistance to fungi and greater resistance against nematodes.

[0138] Increased plant vigor, including plant health / quality and seed vigor, reduced support failure, better appearance, greater recovery after periods of stress, better pigmentation (eg chlorophyll content, permanence effects green, etc.) and better photosynthetic efficiency.

[0139] In addition, the compounds of the formula (I) can reduce the mycotoxin content in the harvested material and in food and feed prepared from it. Mycotoxins include, but are not limited to, the following: deoxynivalenol (DON), nivalenol, 15-AcDON, 3-Ac-DON, T2- and HT2 toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxiscirpenol (DAS), beauvericin, enniatin, fusaroproliferin,

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78/154 fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins that can be produced, for example, by the following fungi: Fusarium species, such as F acuminatum, F asiaticum, F avenaceum, F. crookwellense, F. culmorum, F graminearum (Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani , F. sporotrichoides, F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides etc., and also by Aspergillus species, such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium species, such as P. verrucosum, P. viridicatum, P. citrinum, P. expansion, P. claviforme, P. roqueforti, Claviceps species, such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys species and others.

[0140] The compounds of formula (I) can also be used in the protection of materials, for the protection of materials in industrial installations against attack and destruction by phytopathogenic fungi.

[0141] In addition, the compounds of formula (I) can be used as antifouling compositions, alone or in combinations with other active ingredients.

[0142] Industrial materials in the present context are understood as inanimate materials that have been prepared for use in industry. For example, industrial materials that must be protected by compositions of the invention against microbial alteration or destruction can be adhesives, glues, paper, wallpaper and cardboard / cardboard, textiles, carpets, leather, wood, fibers and fabrics, paints and plastic items, cooling lubricants and other materials that can be infected or destroyed by microorganisms. Parts of production facilities and buildings, for example, cooling water circuits, cooling and heating systems, and ventilation and air conditioning units, which can be adversely affected by the proliferation of

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79/154 microorganisms, can also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, gums, paper and board, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.

[0143] The compounds of formula (I) can prevent adverse effects, such as rot, deterioration, discoloration, fading or mold formation.

[0144] In the case of wood treatment, the compounds of formula (I) can also be used against fungal diseases that can grow on or inside the wood. The term “wood” means all types of wood species and all types of wood work intended for construction, for example, solid wood, high density wood, laminated wood and plywood. The method for treating the wood according to the invention consists essentially of contacting a composition according to the invention; this includes, for example, direct application, spraying, dipping, injection or any other suitable medium.

[0145] In addition, the compounds of the formula (I) can be used to protect objects that come into contact with salt or brackish water, especially hulls, screens, nets, buildings, moorings and signaling systems, to prevent accumulation of dirt.

[0146] The compounds of formula (I) can also be used to protect goods in storage. Storage products are understood to be natural substances of plant or animal origin or products processed from those which are of natural origin, and for which long-term protection is desired.

[0147] Storage products of plant origin, for example, plants or parts of plants, such as stems, leaves, tubers, seeds, fruits,

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80/154 grains, can be protected at harvest or after processing by (pre) drying, humidification, fragmentation, grinding, pressing or roasting. Storage goods also include wood, both unprocessed, as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture. Storage products of animal origin are, for example, fur, leather and fur. The compositions of the invention can prevent adverse effects, such as rotting, deterioration, discoloration, fading or mold formation.

[0148] Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae and sludge organisms. The compounds of formula (I) act preferentially against fungi, especially molds, decolorizing and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against sludge and algae organisms. Examples include microorganisms from the following genera: Alternaria, such as Alternaria tenuis', Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana ', Lentinus, such as Lentinus tigrinus', Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor ', Aureobasidium, such as Aureobasidium pullulans', Sclerophoma, such as Sclerophoma pityophila ', Trichoderma, such as Trichoderma viride', Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Petriella spp. ., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Cladosporium spp., Paecilomyces spp. Mucor spp., Escherichia, such as Escherichia coli ', Pseudomonas, such as Pseudomonas aeruginosa', Staphylococcus, such as Staphylococcus aureus, Candida spp. and Saccharomyces spp., such as Saccharomyces cerevisae.

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81/154 [0149] In addition, the compounds of formula (I) also have very good antimycotic effects. They have a broad spectrum of antimycotic activity, especially against dermatophytes and yeasts, molds and diphasic fungi (for example, against Candida species, such as Candida albicans, Candida glabrata), and Epidermophyton floccosum, Aspergillus species, such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species, such as Trichophyton mentagrophytes, Microsporon species, such as Microsporon canis and audouinii. The listing of these fungi is by no means a restriction of the covered mycotic spectrum, and is merely illustrative. [0150] The compounds can also be used to control important fungal pathogens in fish and crustacean ponds, such as, for example, saprolegnia diclina in trout, or Saprolegnia parasitica in lobster.

[0151] The compounds of formula (I), therefore, can be used in both medical and non-medical applications.

[0152] The compounds of formula (I) can be used as such, in the form of their formulations or as forms of use prepared from them, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dust and granules. The application is carried out in the usual way, for example, by means of irrigation, spraying, atomization, diffusion, dust spreading, foam spreading, spraying and the like. It is also possible to implant the active ingredients using the ultra-low volume method or inject the active ingredient preparation or the ingredient itself into the soil. It is also possible to treat plant seeds.

[0153] It is possible to treat all plants and their parts, according to the invention, preferably with species of wild plants and plant cultivars, or those obtained by conventional biological methods, such as crossing or fusing protoplasts, and also its parts. In another preferred embodiment, transgenic plants and plant cultivars are treated

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82/154 obtained by genetic engineering methods, possibly in combination with conventional methods (Genetically Modified Organisms), and their parts. The terms plant parts or parts or plant parts have been explained above. More preferably, plants of plant cultivars that are commercially available or in use are treated according to the invention. Plant cultivars are understood to be plants that have new properties (characteristics) and were obtained by conventional crossing, by mutagenesis or by recombinant DNA techniques. They can be of cultivars, varieties, biotypes or genotypes.

[0154] The treatment method according to the invention can be used in the treatment of genetically modified organisms (GMOs), for example, plants or seeds. Genetically modified (or transgenic) organisms are plants from which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially means a gene that is supplied or assembled outside the plant and which, when introduced into the nuclear, chloroplastic or mitochondrial genome, gives the transformed plant new or improved agronomic properties or other properties that express a protein or polypeptide of interest or slowing down regulation or silencing other gene (s) present in the plant (using, for example, antisense technology, cosuppression technology, RNA interference-RNAi-technology or microRNA-miRNA technology). A heterologous gene, which is located in the genome is also called a transgene. A transgene that is defined by its location in the plant's genome is called a transgenic transformation or event.

[0155] The plants and plant cultivars that are preferably treated according to the invention include all plants that have genetic material that give useful, particularly advantageous, characteristics to these plants (obtained by means of reproduction and / or biotechnological means) .

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83/154 [0156] Plants and plant cultivars, which are also preferably treated according to the invention, are resistant to one or more biotic stresses, that is, said plants have better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.

[0157] The plants and plant cultivars that can also be treated according to the invention are those plants that are resistant to one or more abiotic stresses. Abiotic stress conditions can include, for example, drought, exposure to cold temperatures, exposure to heat, osmotic stress, flooding, increased soil salinity, increased exposure to minerals, exposure to ozone, high exposure to light, limited availability nitrogen nutrients, limited availability of phosphorus nutrients, shade cancellation.

[0158] The plants and plant cultivars that can also be treated according to the invention, are those plants characterized by improved yield characteristics. The increased yield in said plants may be the result of, for example, better plant physiology, growth and development, such as water use efficiency, water retention efficiency, better nitrogen use, better carbon asymmetry, better photosynthesis , greater efficiency of germination and accelerated maturation. Yield can also be affected by improved plant architecture (under stress and non-stress conditions), including, but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, number and internode distance, root growth, seed size, fruit size, pod size, number of pods or ears, number of seeds per pod or ear, seed mass, improved seed filling, reduced seed dispersion, reduced dehiscence pods and lodging resistance. Other productive features include the

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84/154 seed composition, such as carbohydrate content and composition, for example, cotton or starch, protein content, oil content and composition, nutritional value, reduction of anti-nutritional compounds, better processability and better storage stability.

[0159] The plants that can be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor that generally results in greater productivity, vigor, health and resistance to biotic and abiotic stresses.

[0160] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated according to the invention are herbicide tolerant plants, that is, plants taken tolerant of one or more determined herbicides. Such plants can be obtained by genetic transformation, or by selecting plants containing a mutation conferring such tolerance to the herbicide.

[0161] Plants or plant cultivars (obtained by methods of plant biotechnology such as genetic engineering), which can also be treated according to the invention, are transgenic plants resistant to insects, that is, plants resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selecting plants containing a mutation that confers this resistance to insects.

[0162] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selecting plants containing a mutation conferring such resistance to stress.

[0163] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, show changes in quantity, quality

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85/154 and / or storage stability of the harvested product and / or altered properties of specific ingredients of the harvest product.

[0164] Plants or plant cultivars (which can be obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are plants, such as cotton plants, with fiber characteristics changed. Such plants can be obtained by genetic transformation, or by selecting plants containing a mutation conferring such altered fiber characteristics.

[0165] Plants or plant cultivars (which can be obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are plants, such as rapeseed or related Brassica plants, with characteristics oil profile changes. Such plants can be obtained by genetic transformation, or by selecting plants that contain a mutation conferring such altered oil profile characteristics.

[0166] Plants or plant cultivars (which can be obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are plants, such as oilseed rape or related Brassica plants, with altered seed breaking characteristics. Such plants can be obtained by genetic transformation, or by selecting plants that contain a mutation conferring such altered seed breaking characteristics and include plants such as delayed or reduced seed breaking rape plants.

[0167] Plants or plant cultivars (which can be obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are plants, such as tobacco plants, with altered patterns of modification of post-institutional proteins.

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86/154 [0168] Accordingly, the compounds of the present invention were illustrated in Tables 1 and 2.

[0169] The following tables illustrate in a non-limiting way the examples of compounds according to the invention. In the following examples, M + 1 (or M-1), means the molecular ion peak, about 1 a.m.u. (atomic mass unit) respectively, as seen in exemplos-NMR mass spectroscopy data from selected examples that are written in the form of Ή-NMR peak lists. For each peak of the signal, the value of δ in ppm and the number of protons are listed, in parentheses.

[0170] To calibrate the chemical deviation for the Ή spectra, we use tetramethylsilane and / or the chemical deviation of the solvent used, especially in the case of the spectra measured in DMSO. Therefore, on peak NMR lists, the tetramethylsilane peak may occur, but not necessarily.

[0171] Ή-NMR peak lists are similar to classical Ή-NMR impressions and therefore generally contain all the peaks listed in the classical NMR interpretation.

[0172] In addition, they can present themselves as classic signs of solvent ΉRMN, stereoisomers of target compounds, which are also the subject of the invention, and / or impurity peaks.

[0173] Table 1 provides compounds of general formula (I)

R ⁴ R ²

I I

N

R ⁸

R ⁵ (D

Number

Compound name

Analytical data

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by grade 1. N '- (2,5-dimethyl-4 (phenylamine) phenyl) -N-ethyl-N methylformimidamide Example:! 2. N '- (2,5-dimethyl-4 (methyl (phenyl) amino) phenyl) -Netyl-N-methylformimidamide Example: 2 3. N '- (2-chloro-5-methyl-4 (phenylamine) phenyl) -N-ethyl-N methylformimidamide Example: 3 4. N '- (2-chloro-5-dimethyl-4 (methyl (phenyl) amino) phenyl) -Netyl-N-methylformimidamide Example: 4 5. N '- (2,5-dimethyl-4- (N-phenylmethylsulfonamido) phenyl) N-ethyl-N-methylformimidamide Example: 5 6. N '- (2,5-dimethyl-4- (methyl (2methyl-4- (perfluoropropane-2yl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.5 (s, 1H), 7.36 (s, 1H), 7.14 (s, 1H), 7.12 (s, 1H), 6 , 63 (s, 1H), 6.47 (s, 1H), 3.36 (q, 2H), 3.02 (s, 3H), 2.87 (s, 3H), 2.07 (s, 3H), 1.98 (S, 3H), 1.73 (s, 3H), 1.13 (t, 3H); (M + 1): 478.1 7. N '- (4 - ((4-chlorophenyl) (methyl) amino) -2,5dimethylphenyl) -N-ethyl-N methylformimidamide Example: 6 8. N '- (4 - ((3-chlorophenyl) (methyl) amino) -2,5dimethylphenyl) -N-ethyl-N methylformimidamide Example: 7 9. N '- (4 - ((3,4dichlorophenyl) (methyl) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide Example: 8 10. N '- (2-chloro-5-methyl-4 (methyl (3,4,5trifluorophenyl) amino) phenyl) -Netyl-N-methylformimidamide Example: 9 11. N '- (2-chloro-5-dimethyl-4 (methyl (m-tolyl) amino) phenyl) -Netyl-N-methylformimidamide Example: 10

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12. N '- (2-chloro-4 - ((3,4dichlorophenyl) (methyl) amino) -5 methylphenyl) -N-ethyl-Nmethylformimidamide Example: 11 13. N '- (2-chloro-4 - ((3metfoxyphenyl) (methyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Example: 12 14. N '- (2-chloro-5-methyl-4 (methyl (4 (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Example: 13 ^ -NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.44 (d, 2H), 7.15 (s, 1H), 6.96 (d, 1H) , 6.53 (d, 2H), 3.45-3.35 (m, 2H), 3.18 (s, 3H), 2.97 (s, 3H), 1.97 (s, 3H), 1.14 (t, 3H); (M + 1): 384.15 15. N '- (2-chloro-5-methyl-4 (methyl (p-toli) amino) phenyl) -Netyl-N-methylformimidamide Example: 14 16. N '- (2-chloro-4 - ((2metfoxyphenyl) (methyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Example: 15 17. N '- (2-chloro-5-methyl-4- (N-phenylmethylsulfonamido) phenyl) N-ethyl-N-methylformimidamide Example: 16 18. N '- (2-chloro-4 - ((2-chlorophenyl) (methyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Example: 17 19. N '- (2-chloro-4 - ((4chlorophenyl) (methyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Example: 18 20. N '- (2-chloro-4 - ((4metfoxyphenyl) (methyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Example: 19 21. N '- (2-chloro-4 - ((4-methoxy-3methylphenyl) (methyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Example: 20 22. N '- (2-chloro-4 - ((3,4dimethoxyphenyl) ((methyl)) amino) - Example: 21

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5-methylphenyl) -N-ethyl-N methylformimidamide 23. N '- (2-chloro-4 - ((3,5-dimethoxyphenyl) ((methyl)) amino) 5-methylphenyl) -N-ethyl-N methylformimidamide Example: 22 24. N '- (2,5-dimethyl-4 - ((methyl) (mtolyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.74 (s, 1H), 7.09 (s, 1H), 6.95 (t, 1H), 6.85 (s, 1H), 6 , 64 (s, 1H), 6.44-6.41 (m, 3H), 3.37 (q, 2H), 2.92 (s, 3H), 2.15 (s, 3H), 2, 09 (s, 3H), 2.06 (s, 3H), 1.12 (t, 3H; (M + 1): 310.2 25. N-ethyl-N '- (4 - ((3methoxyphenyl) ((methyl)) amino) 2,5-dimethylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.78 (s, 1H), 6.98 (t, 1H), 6.85 (s, 1H), 6.77 (s, 1H), 6 , 20 (dd, 1H), 6.00 (dd, 1H), 5.95 (t, 1H), 3.62 (d, 3H), 3.45-3.40 (m, 2H), 3, 10 (s, 3H), 3.02 (s, 3H), 2.13 (s, 3H), 1.97 (s, 3H), 1.14 (t, 3H); (M + l): 326, l 26. N '- (2,5-dimethyl-4 - ((methyl) (ptolyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 6.90 (d, 2H), 6.81 (s, 1H), 6.72 (s, 1H), 6 , 34 (d, 2H), 3.37 (q, 2H), 3.08 (s, 3H), 2.99 (s, 3H), 2.07 (s, 6H), 1.96 (s, 3H), 1.13 (t, 3H); (M + l): 310, l 27. N-ethyl-N '- (4 - ((4methoxyphenyl) ((methyl)) amino) 2,5-dimethylphenyl) -Nmethylformimidamide Example: 24 28. N-ethyl-N '- (4 - ((3methoxyphenyl) amino) -2,5dimethylphenyl) -Nmethylformimidamide Example: 23 29. N '- (2,5-dimethyl-4- (mtolylamino) phenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.74 (s, 1H), 7.09 (s, 1H), 6.95 (t, 1H), 6.85 (s, 1H), 6 , 64 (s, 1H), 6.44-6.41 (m, 3H), 3.37 (q, 2H), 2.92 (s, 3H), 2.15 (s, 3H), 2, 09 (s, 3H), 2.06 (s, 3H), 1.12 (t, 3H); (M + 1): 295.8 30. N '- (2,5-dimethyl-4- (ptolylamino) phenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.58 (s, 1H), 6.95-6.83 (m, 4H), 6.60-6.56 (m, 3H), 3, 40-3.37 (m, 2H), 2.91 (s, 3H), 2.15 (s, 3H), 2.06 (s, 6H), 1.11 (t, 3H); (M + 1): 296.4 31. N '- (4 - ((4- (tertbutyl) phenyl) ((methyl)) amino) - ^X H-NMR (400 MHz, DMSO-d6) δ 7.62 (s, 1H), 7.07 (q, 2H), 6.75 (d, 1H), 6.65 (s, 1H),

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2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide 6.32 (q, 2H), 3.28 (q, 2H), 3.04 (s, 3H), 2.89 (s, 3H), 2.06 (s, 3H), 1.94 (s , 3H), 1.17 (s, 9H), 1.09 (t, 3H); (M + l): 352, l 32. N '- (4 - ((4- (tertbutyl) phenyl) amino) -2,5dimethylphenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.67 (s, 1H), 7.14-7.10 (m, 2H), 6.97 (s, 1H), 6.86 (s, 1H), 6.63-6.60 (m, 3H), 3.36 (q, 2H), 2.91 (s, 3H), 2.07 (s, 6H), 1.19 (s, 9H ), 1.11 (t, 3H); (M + 1): 338.4 33. N '- (4 - ((2-chlorophenyl) (methyl) amino) -2,5dimethylphenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.59 (s, 1H), 7.33 (dd, 1H), 7.26-7.22 (m, 1H), 7.036.95 (m, 2H), 6.60 (d, 2H), 3.35 (q, 2H), 3.02 (s, 3H), 2.89 (s, 3H), 2.04 (s, 3H), 1, 98 (s, 3H), 1.08 (t, 3H); (M + 1): 330.2 34. N '- (2-chloro-4 - ((2-chlorophenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.69 (s, 1H), 7.32 (dd, 1H), 7.09-7.03 (m, 3H), 6.89 (s, 1H), 6.70 (td, 1H), 6.39 (dd, 1H), 3.493.28 (m, 2H), 2.96 (s, 3H), 2.05 (s, 3H), 1, 13 (t, 3H); (M + 1): 336.55 35. N-ethyl-N '- (4 - ((2 fluorophenyl) amino) -2,5dimethylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.66 (s, 1H), 7.37-7.11 (m, 4H), 7.02 (d, 1H), 6.806.78 (m, 1H), 6.69 (d, 1H), 3.41-3.33 (m, 2H), 2.91 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H ), 1.96 (s, 3H), 1.11 (t, 3H); (M + 1): 300.15 36. N-ethyl-N '- (4 - ((2 fluorophenyl) ((methyl)) amino) 2,5-dimethylphenyl) -Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.60 (s, 1H), 7.04-6.97 (m, 2H), 6.84-6.79 (m, 2H), 6, 72 (s, 1H), 6.60 (s, 1H), 3.35-3.25 (m, 2H), 3.06 (s, 3H), 2.91 (s, 3H), 2.06 (s, 3H), 2.02 (s, 3H), 1.11 (t, 3H); (M + 1): 314.30 37. N '- (2-chloro-4 - ((2-fluorophenyl) (methyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.66 (s, 1H), 7.08-7.03 (m, 2H), 6.94 (s, 1H), 6.926.87 (m, 2H), 6.83 (s, 1H), 3.38-3.24 (m, 2H), 3.07 (s, 3H), 2.94 (s, 3H), 2.02 (s, 3H ), 1.12 (t, 3H); (M + 1): 334.05 38. N-ethyl-N '- (4 - ((3 fluorophenyl) ((methyl)) amino) 2,5-dimethylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, CHLOROFORM-D) δ 7.47 (s, 1H), 7.06 (td, 1H), 6.88 (s, 1H), 6.67 (s, 1H), 6 , 36-6.31 (m, 1H), 6.25 (dd, 1H), 6.18 (dt, 1H), 3.61-3.25 (m, 2H), 3.18 (s, 3H ), 3.03 (s, 3H), 2.22 (s, 3H), 2.05 (s, 3H), 1.21 (t, 3H); (M + 1): 314.35 39. N-ethyl-N '- (4 - ((4 fluorophenyl) ((methyl)) amino) - ^X H-NMR (400 MHz, CHLOROFORM-D) δ 7.46 (s, 1H), 6.82-6.78 (m, 3H), 6.65 (s, 1H),

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2,5-dimethylphenyl) -Nmethylformimidamide 6.41-6.34 (m, 2H), 3.48-3.32 (m, 2H), 3.16 (s, 3H), 3.01 (s, 3H), 2.20 (s, 3H), 2.03 (s, 3H), 1.22 (t, 3H); (M + 1): 314.15 40. N '- (4 - ((2-chlorophenyl) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide Example: 25 41. N- (4- (((ethyl ((methyl)) amino) methylene) amino) -2,5-dimethylphenyl) -Nphenylacetamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.64 (s, 1H), 7.26-7.06 (m, 6H), 6.66 (s, 1H), 3,373.28 (m, 2H), 2.87 (s, 3H), 2.10 (s, 6H), 1.95 (s, 3H), 1.12 (t, 3H); (M + l): 324, l 42. N '- (2-chloro-5- (methyl) -4 ((methyl) (pyridine-2yl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 8.10 (s, 1H), 7.72 (d, 1H), 7.39-7.34 (m, 1H), 7.15 (s, 1H), 6.94 (d, 1H), 6.58 (dd, 1H), 6.05 (d, 1H), 3.46-3.34 (m, 2H), 3.25 (s, 3H ), 3.00 (s, 3H), 1.97 (s, 3H), 1.14 (t, 3H); (M + 1): 318.10 43. N '- (4 - ((4-chlorophenyl) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.63 (s, 1H), 7.39 (s, 1H), 7.11-7.08 (m, 2H), 6.85 (s, 1H), 6.65 (s, 1H), 6.62-6.58 (m, 2H), 3.37 (q, 2H), 2.92 (s, 3H), 2.10 (s, 3H ), 2.05 (s, 3H), 1.12 (t, 3H); (M + 1): 316.10 44. N-ethyl-N '- (4 - ((4 fluorophenyl) amino) -2,5dimethylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, CHLOROFORM-D) δ 7.43 (s, 1H), 6.92-6.86 (m, 3H), 6.75-6.71 (m, 2H), 6, 64 (s, 1H), 5.55-4.48 (m, 1H), 3.39-3.43 (m, 2H), 3.02 (s, 3H), 2.22 (s, 3H) , 2.15 (s, 3H), 1.24 (t, 3H); (M + l): 300.25 45. N-ethyl-N '- (4 - ((2methoxyphenyl) amino) -2,5dimethylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, CHLOROFORM-D) δ 7.45 (s, 1H), 7.05 (s, 1H), 6.86-6.70 (m, 4H), 6.64 (s, 1H), 5.71 (s, 1H), 3.91 (s, 3H), 3.39-3.38 (m, 2H), 3.02 (s, 3H), 2.22 (s, 3H ), 2.17 (s, 3H), 1.20 (t, 3H); (M + 1): 312.20 46. N-ethyl-N '- (4 - ((3 fluorophenyl) amino) -2,5dimethylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, CHLOROFORM-D) δ 7.44 (s, 1H), 7.10 (dd, 1H), 7.00 (s, 1H), 6.68 (s, 1H), 6 , 50-6.37 (m, 3H), 5.33 (s, 1H), 3.43- 3.37 (m, 2H), 3.21 (s, 3H), 2.20 (s, 3H ), 2.16 (s, 3H), 1.19 (t, 3H); (M + 1): 300.10 47. N '- (2-chloro-4 - ((2-fluorophenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, CHLOROFORM-D) δ 7.53 (s, 1H), 7.23 (s, 1H), 7.05 (ddd, 1H), 6.96 (t, 1H), 6 , 85-6.73 (m, 3H), 5.38 (s, 1H), 3.36 (q, 2H), 3.08 (s, 3H), 2.21 (s, 3H), 1, 29 - 1.23 (m, 3H); (M + 1): 320, 1 48. N '- (2-chloro-4 - ((3- Example: 26

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chlorophenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide 49. N- (3-chlorophenyl) -N, 2,5-trimethyl-4 ((morpholinomethylene) amino) aniline Example: 28 50. N '- (2-chloro-4 - ((3-chlorophenyl) (methyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Example: 27 51. N- (3-chlorophenyl) -N, 2, 5- trimethyl-4 - (((piperidine-1 ylmethylene) amino) aniline Example: 29 52. N-allyl-N '- (4 - ((3-chlorophenyl) ((methyl)) amino) -2,5dimethylphenyl) -Nmethylformimidamide Example: 31 53. N '- (4 - ((3-chlorophenyl) ((methyl)) amino) -2,5dimethylphenyl) -N-isopropyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.67 (s, 1H), 7.11-7.07 (m, 1H), 6.83 (s, 1H), 6.71 (s, 1H), 6.60-6.58 (m, 1H), 6.36-6.35 (m, 2H), 3.79-3.65 (m, 1H), 3.11 (s, 3H) , 2.83 (s, 3H), 2.12 (s, 3H), 1.95 (s, 3H), 1.22 (d, 6H); (M + 1): 344.4 54. N '- (4 - ((2-bromophenyl) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.63 (s, 1H), 7.46-7.43 (m, 2H), 7.26-7.13 (m, 1H), 7, 08-7.04 (m, 1H), 6.86 (s, 1H), 6.66 (d, 2H), 6.59-6.55 (m, 1H), 6.32 (dd, 1H) , 2.93 (s, 3H), 2.14 (s, 3H), 2.02 (s, 3H), 1.15 (t, 3H); (M + 1): 362.0 55. N '- (4 - ((3-chlorophenyl) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, CHLOROFORM-D) δ 7.45 (s, 1H), 7.06 (t, 1H), 6.97 (s, 1H), 6.70- 6.68 (m, 2H), 6.64 (d, 1H), 6.56 (dd, 1H), 6.27 (s, 1H), 3.37-3.33 (m, 2H), 3.01 (s, 3H ), 2.22 (s, 3H), 2.14 (s, 3H), 1.22 (t, 3H); (M + 1): 316.10 56. N-ethyl-N '- (4 - ((4methoxyphenyl) amino) -2,5dimethylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.57 (s, 1H), 6.78-6.66 (m, 6H), 6.59 (s, 1H), 3.65 (s, 3H), 3.44-3.33 (m, 2H), 2.90 (s, 3H), 2.07 (s, 3H), 2.01 (s, 3H), 1.11 (t, 3H ); (M + 1): 312.0 57. N '- (2,5-dimethyl-4 - ((2- ^X H-NMR (400 MHz, DMSO-d6) δ 7.65 (s,

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(trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide 1H), 7.46-7.44 (m, 1H), 7.26 (t, 1H), 6.91 (s, 1H), 6.87 (s, 1H), 6.73-6.69 (m, 2H), 6.36 (d, 1H), 3.35-3.29 (m, 2H), 2.93 (s, 3H), 2.11 (s, 3H), 1.99 (s, 3H), 1.10 (t, 3H) ); (M + l): 350.30 58. N '- (2,5-dimethyl-4 - ((methyl) (2 (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.51-7.42 (m, 3H), 7.15 (dd, 2H), 6.65 (s, 1H), 6.56 (s, 1H), 3.35-3.29 (m, 2H), 3.08 (s, 3H), 2.90 (s, 3H), 2.06 (s, 3H), 1.95 (s, 3H ), 1.10 (t, 3H); (M + 1): 364.15 59. N '- (2,5-dimethyl-4 - ((4 (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.89 (s, 1H), 7.62 (s, 1H), 7.37 (d, 2H), 6.88 (s, 1H), 6 , 67-6.64 (m, 3H), 3.35 (q, 2H), 2.92 (s, 3H), 2.11 (s, 3H), 2.06 (s, 3H), 1, 12 (t, 3H); (M + 1): 350.15 60. N '- (2,5-dimethyl-4 - ((3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.64 (s, 1H), 7.16 (t, 1H), 6.87 (s, 1H), 6.66 (s, 1H), 6 , 58 (dd, 2H), 6.49 (dd, 1H), 6.43 (d, 1H), 3.39-3.35 (m, 2H), 2.92 (s, 3H), 2, 10 (s, 3H), 2.05 (s, 3H), 1.12 (t, 3H); (M + 1): 366.15 61. N '- (2,5-dimethyl-4 - ((methyl) (4 (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.67 (s, 1H), 7.40 (d, 2H), 6.85 (s, 1H), 6.73 (s, 1H), 6 , 51 (d, 2H), 3.39-3.34 (m, 2H), 3.17 (s, 3H), 2.93 (s, 3H), 2.12 (s, 3H), 1, 95 (s, 3H), 1.12 (t, 3H); (M + 1): 364.35 62. N '- (2,5-dimethyl-4 - ((methyl) (3 (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.66 (s, 1H), 7.18 (t, 1H), 6.85 (s, 1H), 6.71 (s, 1H), 6 , 52-6.50 (m, 1H), 6.40 (dd, 1H), 6.24 (s, 1H), 3.37-3.31 (m, 2H), 3.13 (s, 3H ), 2.92 (s, 3H), 2.11 (s, 3H), 1.95 (s, 3H), 1.12 (t, 3H); (M + 1): 380.35 63. N '- (2,5-dimethyl-4 - ((3- (methylthio) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.61 (s, 1H), 7.27 (s, 1H), 7.01 (t, 1H), 6.86 (s, 1H), 6 , 63 (s, 1H), 6.50-6.47 (m, 2H), 6.40-6.37 (m, 1H), 3.54-3.26 (m, 2H), 2.91 (s, 3H), 2.35 (s, 3H), 2.10 (s, 3H), 2.06 (s, 3H), 1.11 (t, 3H); (M + 1): 328.15 64. N '- (4 - ((2bromophenyl) ((methyl)) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-D6) δ 7.58-7.53 (m, 2H), 7.30-7.26 (m, 1H), 6.99 (dd, 1H), 6, 92 (td, 1H), 6.64 (s, 1H), 6.57 (s, 1H), 3.353.21 (m, 2H), 3.02 (s, 3H), 2.90 (s, 3H ), 2.07 (s, 3H), 1.95 (s, 3H), 1.10 (t, 3H); (M + l):

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376.05 65. N-ethyl-N '- (4 - ((2methoxyphenyl) ((methyl)) amino) 2,5-dimethylphenyl) -Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.57 (s, 1H), 6.88-6.84 (m, 2H), 6.74-6.71 (m, 2H), 6, 60 (dd, 1H), 6.52 (s, 1H), 3.67 (s, 3H), 3.47-3.33 (m, 2H) 3.02 (s, 3H), 2.90 ( s, 3H), 2.10 (s, 3H), 1.83 (s, 3H), 1.10 (t, 3H); (M + 1): 326.35 66. N '- (2,5-dimethyl-4 - ((methyl) (3 (methylthio) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.66 (s, 1H), 7.03 (t, 1H), 6.81 (s, 1H), 6.69 (s, 1H), 6 , 49 (dd, 1H), 6.28 (t, 1H), 6.18 (dd, 1H), 3.54-3.26 (m, 2H), 3.11 (s, 3H), 2, 92 (s, 3H), 2.40 (s, 3H), 2.11 (s, 3H), 1.95 (s, 3H), 1.12 (t, 3H); (M + 1): 342.25 67. N '- (2-chloro-5- (methyl) -4 - ((3 (methylthio) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.42 (s, 1H), 7.09-7.04 (m, 2H), 6.85 (s, 1H), 6.57-6.56 (m, 2H), 6.47-6.45 (m, 1H), 3.47-3.45 (m, 2H), 2.94 (s, 3H) , 2.38 (s, 3H), 2.08 (s, 3H), 1.13 (t, 3H); (M + 1): 348.10 68. N '- (2-chloro-5- (methyl) -4- (mtolylamino) phenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.76 (s, 1H), 7.30-7.14 (m, 1H), 7.08-6.89 (m, 2H), 6, 89-6.71 (m, 1H), 6.56-6.38 (m, 3H), 3.513.19 (m, 2H), 3.04 (s, 3H), 2.19 (s, 6H) , 1.20 (t, 3H); (M + 1); 316.1 69. N '- (2-chloro-4 - ((3-methoxyphenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.66 (s, 1H), 7.34 (s, 1H), 7.06-7.01 (m, 2H), 6.84 (s, 1H), 6.30-6.24 (m, 3H), 3.65 (s, 3H), 3.47-3.36 (m, 2H), 2.94 (s, 3H), 2.09 (s, 3H), 1.12 (t, 3H); (M + l): 332, l 70. N '- (2-chloro-5- (methyl) -4- (otolylamino) phenyl) -N-ethyl-N methylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.70 (s, 1H), 7.09 (d, 1H), 6.97-7.91 (m, 1H), 6.83 (s, 1H), 6.78 (s, 1H), 6.73 (td, 1H), 6.61 (s, 1H), 6.46 (d, 1H), 3.34-3.22 (m, 2H ), 2.94 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 1.16 (t, 3H); (M + 1): 316.10 71. N '- (2-chloro-4 - ((4-chlorophenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.66 (d, 1H), 7.53 (s, 1H), 7.15 (d, 2H), 7.05 (s, 1H), 6 , 86 (s, 1H), 6.67 (d, 2H), 3.44-3.36 (m, 2H), 2.94 (s, 3H), 2.08 (s, 3H), 1, 12 (t, 3H): (M + 1): 337.10 72. N '- (2,5-dimethyl-4- (otolylamino) phenyl) -N-ethyl-N - ¹ H-NMR (400 MHz, DMSO-d6) δ 7.60 (s, 1H), 7.03 (d, 1H), 6.92-6.88 (m, 1H), 6.72 (s,

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methylformimidamide 1H), 6.63-6.57 (m, 2H), 6.39 (s, 1H), 6.30 (d, 1H), 3.39-3.33 (m, 2H), 2.92 (s, 3H), 2.18 (s, 3H), 2.09 (s, 3H), 2.02 (s, 3H ), 1.12 (t, 3H); (M + 1): 296.20 73. N '- (2-chloro-4 - ((4 methoxyphenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.67 (s, 1H), 6.92 (s, 1H), 6.89 (s, 1H), 6.84-6.78 (m, 5H), 3.40-3.37 (m, 2H), 3.33 (s, 3H), 2.90 (s, 3H), 2.09 (s, 3H), 1.15-1.10 (t, 3H); (M + 1): 332.15 74. N '- (2-chloro-5- (methyl) -4 ((methyl) (o-tolyl) amino) phenyl) N-ethyl-N-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.69 (s, 1H), 7.13 (t, 2H), 6.96-6.91 (m, 2H), 6.80 (s, 1H), 6.74 (s, 1H), 3.37 (q, 2H), 2.93 (s, 6H), 1.96 (s, 6H), 1.11 (t, 3H); (M + 1): 330.20 75. N '- (4 - ((2-bromophenyl) amino) - 2-chloro-5-methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.68 (s, 1H), 7.49 (dd, 1H), 7.13-7.09 (m, 1H), 7.03 (s, 1H), 6.88 (d, 2H), 6.65 (td, 1H), 6.39 (dd, 1H), 3.46-3.36 (m, 2H), 2.96 (s, 3H ), 2.03 (s, 3H), 1.16 (t, 3H); (M + 1): 381.95 76. N '- (4 - ((2bromophenyl) ((methyl)) amino) -2chloro-5-methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.70 (s, 1H), 7.59-7.57 (m, 1H), 7.33 (t, 1H), 7.036.96 (m, 2H), 6.83 (s, 1H), 6.79 (s, 1H), 3.403.28 (m, 2H), 3.02 (s, 3H), 2.90 (s, 3H), 1, 93 (s, 3H), 1.11 (t, 3H); (M + 1): 395.7 77. N '- (2,5-dimethyl-4 - ((methyl) (otolyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.57 (s, 1H), 7.14-7.10 (m, 1H), 7.06-7.05 (m, 1H), 6, 94-6.92 (m, 1H), 6.87 (td, 1H), 6.58 (s, 1H), 6.52 (s, 1H), 3.53-3.33 (m, 2H) , 2.96 (s, 3H), 2.89 (s, 3H), 2.02 (s, 6H), 1.86 (s, 3H), 1.10 (t, 3H); (M + 1): 310.25 78. N '- (2-chloro-4 - ((2methoxyphenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 6.98 (s, 1H), 6.94-6.91 (m, 1H), 6.84 (s, 1H), 6.76-6.69 (m, 2H), 6.54 (s, 1H), 6.46 (dd, 1H), 3.81 (s, 3H), 3.34 (q, 2H ), 2.94 (s, 3H), 2.07 (s, 3H), 1.12 (t, 3H); (M + 1): 332.1 79. N '- (2-chloro-5-methyl-4 - ((2 (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.70 (d, 1H), 7.50 (dd, 1H), 7.32 (t, 1H), 7.09 (d, 2H), 6 , 90 (d, 1H), 6.81 (t, 1H), 6.40 (d, 1H), 3.44-3.35 (m, 2H), 2.96 (s, 3H), 1, 98 (s, 3H), 1.12 (t, 3H); (M + 1): 370.15 80. N '- (2-chloro-5-methyl-4- (methyl (2- ^X H-NMR (400 MHz, DMSO-d6) δ 7.70-7.57 (m, 3H), 7.26-7.22 (m, 2H), 6.80-6.77 (m,

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(trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide 2H), 3.40-3.26 (m, 2H), 3.08 (s, 3H), 2.93 (s, 3H), 1.96 (s, 3H), 1.11 (t, 3H ); (M + 1): 384.20 81. N '- (2-chloro-5- (methyl) -4 - ((4 (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 8.03 (s, 1H), 7.69 (d, 1H), 7.43 (d, 2H), 7.11 (s, 1H), 6 , 90 (d, 1H), 6.71 (d, 2H), 3.44-3.35 (m, 2H), 2.95 (s, 3H), 2.08 (s, 3H), 1, 13 (t, 3H); (M + 1): 370.05 82. N '- (2-chloro-4 - ((3-fluorophenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.61 (s, 2H), 7.13 (dd, 1H), 7.08 (s, 1H), 6.88 (s, 1H), 6 , 48 (dd, 1H), 6.45-6.40 (m, 1H), 6.34 (dt, 1H), 3.43-3.36 (m, 2H), 2.95 (s, 3H ), 2.08 (s, 3H), 1.14 (t, 3H); (M + l): 320.10 83. N '- (2-chloro-4 - ((4-fluorophenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.64 (s, 1H), 7.27 (s, 1H), 7.02-6.96 (m, 3H), 6.84 (s, 1H), 6.76-6.72 (m, 2H), 3.40-3.32 (m, 2H), 2.93 (s, 3H), 2.09 (s, 3H), 1.16 (t, 3H); (M + 1): 320.05 84. N '- (2-chloro-4 - ((3 fluorophenyl) ((methyl)) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.14-7.08 (m, 2H), 6.94 (d, 1H), 6,436.38 (m, 1H ), 6.21-6.17 (m, 2H), 3.45-3.36 (m, 2H), 3.12 (s, 3H), 3.00 (s, 3H), 1.98 ( s, 3H), 1.14 (t, 3H); (M + 1): 334.15 85. N '- (2-chloro-4 - ((4 fluorophenyl) ((methyl)) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 7.07 (s, 1H), 6.99-6.90 (m, 3H), 6,456.42 (m, 2H ), 3.40-3.25 (m, 2H), 3.10 (s, 3H), 2.96 (s, 3H), 1.98 (s, 3H), 1.13 (t, 3H) ; (M + 1): 334.20 86. N '- (2,5-dimethyl-4 - ((3 (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 7.63 (s, 1H), 7.27 (t, 1H), 6.88-6.80 (m, 4H), 6.67 (s, 1H), 3.40-3.34 (m, 2H), 2.92 (s, 3H), 2.11 (s, 3H), 2.05 (s, 3H), 1.12 (t, 3H); (M + 1): 350.15 87. N '- (2-chloro-5- (methyl) -4 - ((3 (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.85 (s, 1H), 7.69 (d, 1H), 7.33 (t, 1H), 7.08 (d, 1H), 6.96-6.87 (m, 4H), 3.46-3.35 (m, 2H), 2.95 (s, 3H), 2.08 (s, 3H), 1.11 (t, 3H); (M + 1): 370.10 88. N '- (2-chloro-5-methyl-4 (methyl (3 (trifluoromethyl) phenyl) amino) fen Ή-NMR (400 MHz, DMSO-d6) δ 7.74 (s, 1H), 7.33 (t, 1H), 7.15 (s, 1H), 6.97-6.93 (m, 2H ), 6.69-6.64 (m, 2H), 3.46-3.33 (m, 2H),

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il) -N-ethyl-Nmethylformimidamide 3.18 (s, 3H), 2.97 (s, 3H), 1.97 (s, 3H), 1.14 (t, 3H); (M + 1): 384.15 89. N '- (2,5-dimethyl-4 - ((methyl) (3 (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.68 (s, 1H), 7.29 (t, 1H), 6.88-6.85 (m, 2H), 6.72 (s, 1H), 6.66-6.60 (m, 2H), 3.41-3.39 (m, 2H), 3.16 (s, 3H), 2.95 (s, 3H), 2.11 (s, 3H), 1.94 (s, 3H), 1.12 (t, 3H); (M + 1): 364.30 90. N '- (4 - ((2,6difluorophenyl) amino) -2,5dimethylphenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.55 (s, 1H), 7.07-6.95 (m, 3H), 6.56 (d, 2H), 6.31 (s, 1H), 3.35-3.29 (m, 1H), 2.89 (s, 3H), 2.16 (s, 3H), 2.00 (s, 3H), 1.10 (t, 3H ); (M + 1): 318.35 91. N '- (2-chloro-4 - ((2,6difluorophenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.61 (s, 1H), 7.15-7.05 (m, 3H), 6.80 (d, 2H), 6.39 (s, 1H), 3.35-3.31 (m, 2H), 2.88 (s, 3H), 2.18 (s, 3H), 1.10 (t, 3H); (M + 1): 338.1 92. N '- (4 - ((2,6difluorophenyl) ((methyl)) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.55-7.49 (m, 1H), 7.10-6.96 (m, 3H), 6.84 (s, 1H), 6, 49 (s, 1H), 3.35-3.24 (m, 2H), 3.18 (s, 3H), 2.89 (s, 3H), 2.15 (s, 3H), 1.86 (s, 3H), 1.10 (t, 3H); (M + 1): 332.35 93. N '- (2-chloro-4 - ((2,6difluorophenyl) ((methyl)) amino) 5-methylphenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.62 (s, 1H), 7.16-7.11 (m, 1H), 7.07-7.02 (m, 3H), 6, 70 (s, 1H), 3.47-3.34 (m, 2 H), 3.17 (s, 3H), 2.92 (s, 3H), 1.79 (s, 3H), 1, 10 (t, 3H); (M + 1): 352.15 94. N '- (4 - ((2-chloro-6fluorophenyl) amino) -2,5dimethylphenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.55 (s, 1H), 7.30-7.28 (m, 1H), 7.18 (d, 1H), 7.01 (td, 1H), 6.55 (s, 1H), 6.47 (s, 1H), 6.22 (s, 1H), 3.35-3.28 (d, 2H), 2.89 (s, 3H ), 2.16 (s, 3H), 1.99 (s, 3H), 1.10 (t, 3H); (M + 1): 334.7 95. N '- (2-chloro-4 - ((2-chloro-6 fluorophenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.66 (s, 1H), 7.35 (d, 1H), 7.28-7.23 (m, 1H), 7.13 (td, 1H), 6.78 (d, 2H), 6.27 (s, 1H), 3.39-3.34 (m, 2H), 2.91 (s, 3H), 2.18 (s, 3H ), 1.11 (t, 3H); (M + 1): 354.1 96. N '- (4 - ((2-chloro-6fluorophenyl) ((methyl)) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.55 (s, 1H), 7.31-7.28 (m, 1H), 7.18-7.14 (m, 2H), 6, 81 (s, 1H), 6.46 (s, 1H), 3.35 - 3.28 (d, 2H), 3.14 (s, 3H), 2.89 (s, 3H), 2.11 (s, 3H), 1.76 (s, 3H), 1.09 (t, 3H); (M + 1): 348.65 97. N '- (2,5-dimethyl-4 - ((4- ^X H-NMR (400 MHz, DMSO-d6) δ 8.05 (s,

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(pentafluoro-16sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide 1H), 7.64-7.53 (m, 3H), 6.89 (s, 1H), 6.68 (s, 1H), 6.59 (d, 2H), 3.49-3.32 (m, 2H), 2.92 (s, 3H), 2.11 (s, 3H), 2.05 (s, 3H ), 1.12 (t, 3H); (M + 1): 408.15 98. N '- (4 - ((2,6-dichloro-4 (trifluoromethyl) phenyl) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.73 (s, 2H), 7.61-7.59 (m, 1H), 7.16 (s, 1H), 6.58 (s, 1H), 6.35 (s, 1H), 3.41-3.35 (m, 2H), 2.88 (s, 3H), 2.11 (s, 3H), 1.99 (s, 3H ), 1.08 (t, 3H); (M + 1): 418.10 99. N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.63 (s, 1H), 7.21-7.17 (m, 2H), 7.05-7.01 (m, 1H), 6, 83 (s, 1H), 6.67-6.61 (m, 2H), 6.35 (dd, 1H), 3.35 (s, 2H), 2.92 (s, 3H), 2.11 (s, 3H), 2.02 (s, 3H), 1.12 (t, 3H); (M + l): 366, l 100. N '- (2-chloro-5- (methyl) -4 - ((2 (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.69 (s, 1H), 7.39 (s, 1H), 7.23-7.21 (m, 1H), 7,117.07 (m, 1H), 7.01 (s, 1H), 6.90 (s, 1H), 6.776.70 (m, 1H), 6.42 (dd, 1H), 3.43-3.34 (m, 2H ), 2.96 (s, 3H), 2.04 (s, 3H), 1.13 (t, 3H); (M + 1): 386.65 101. N '- (2-chloro-5- (methyl) -4 - ((3 (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.79-7.62 (m, 2H), 7.21 (t, 1H), 7.09 (s, 1H), 6.89 (s, 1H), 6.65-6.51 (m, 3H), 3.44-3.35 (m, 2H), 2.95 (s, 3H), 2.08 (s, 3H), 1.13 (t, 3H); (M + 1): 386.40 102. N '- (2,5-dimethyl-4 - ((4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.60 (s, 1H), 7.45 (s, 1H), 7.06 (d, 2H), 6.87 (s, 1H), 6 , 64-6.61 (m, 3H), 3.35-3.31 (m, 2H), 2.91 (s, 3H), 2.10 (s, 3H), 1.98 (s, 3H) ), 1.11 (t, 3H); (M + 1): 366.05 103. N '- (2-chloro-5- (methyl) -4 - ((4 (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.66 (d, 2H), 7.12 (d, 2H), 7.08 (s, 1H), 6.87 (s, 1H), 6 , 73-6.69 (m, 2H), 3.42-3.33 (m, 2H), 2.95 (s, 3H), 2.10 (s, 3H), 1.13 (t, 3H ); (M + 1): 386.35 104. N '- (2,5-dimethyl-4 - ((methyl) (2 (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.59 (s, 1H), 7.26-7.22 (m, 1H), 7.17-7.15 (m, 1H), 7, 00 (dd, 1H), 6.94-6.90 (m, 1H), 6.60 (d, 2H), 3.35-3.31 (m, 2H), 3.07 (s, 3H) , 2.91 (s, 3H), 2.04 (s, 3H), 1.98 (s, 3H), 1.10 (t, 3H); (M + 1): 380.15

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105. N '- (2-chloro-5-methyl-4 (methyl (2 (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.65 (s, 1H), 7.31-7.27 (m, 1H), 7.21-7.19 (m, 1H), 7.10 (dd, 1H), 7, O2- 6.97 (m, 1H), 6.85 (s, 1H), 6.79 (s, 1H), 3.42-3.32 (m, 2H), 3.06 (s, 3H), 2.98 (s, 3H), 2.06 (s, 3H ), 1.12 (t, 3H); (M + 1): 400.65 106. N '- (2,5-dimethyl-4 - ((methyl) (4 (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.66 (s, 1H), 7.08 (d, 2H), 6.83 (s, 1H), 6.70 (s, 1H), 6.43 (dd, 2H), 3.34-3.29 (m, 2H), 3.12 (s, 3H), 2.92 (s, 3H), 2.11 (s, 3H), 1.96 (s, 3H), 1.12 (t, 3H); (M + l): 380.10 107. N '- (2-chloro-5- (methyl) -4 ((methyl) (4 (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 7.12-7.10 (m, 3H), 6.94 (d, 1H), 6,496.45 (m, 2H ), 3.45-3.32 (m, 2H), 3.13 (s, 3H), 2.93 (s, 3H), 1.98 (s, 3H), 1.14 (t, 3H) ; (M + 1): 400.70 108. N '- (2-chloro-5- (methyl) -4 ((methyl) (3 (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.21 (t, 1H), 7.14 (s, 1H), 6.95 (d, 1H), 6, 57 (d, 1H), 6.42 (dd, 1H), 6.28 (s, 1H), 3.45-3.33 (m, 2H), 3.15 (s, 3H), 2.97 (s, 3H), 1.97 (s, 3H), 1.14 (t, 3H); (M + 1): 400.60 109. N '- (2-chloro-5- (methyl) -4- (Nphenylethylsulfonamido) phenyl) -N-ethyl-N-methylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 7.57 (s, 1H), 7.36-7.34 (m, 4H), 7,237.16 (m, 1H ), 6.90 (d, 1H), 3.33 (m, 4H), 2.96 (s, 3H), 2.18 (s, 3H), 1.22 (s, 3H), 1.13 (t, 3H); (M + 1): 394.35 110. N '- (2-chloro-4 - ((2,4-dichloro-6 (trifluoromethyl) phenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.82 (s, 2H), 7.71 (s, 1H), 7.36 (s, 1H), 6.82 (s, 1H), 6.50 (s, 1H), 3.34 (q, 2H), 2.94 (s, 3H), 2.16 (s, 3H), 1.12 (t, 3H); (M + 1): 439.95 111. N '- (2-chloro-5- (methyl) -4 - ((4 (pentafluoro-16sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 8.17 (s, 1H), 7.69 (d, 1H), 7.59 (d, 2H), 7.12 (s, 1H), 6.92 (s, 1H), 6.65 (d, 2H), 3, 43-3.34 (m, 2H), 2.96 (s, 3H), 2.08 (s, 3H), 1.13 (t, 3H); (M + 1): 428.0 112. N '- (2-chloro-4 - ((2-chloro-6fluorophenyl) ((methyl)) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.61 (s, 1H), 7.34 (dd, 1H), 7.26-7.24 (m, 2H), 7.03 (s, 1H ), 6.68 (s, 1H), 3.39-3.24 (m, 2H), 3.16 (s, 3H), 2.92 (s, 3H), 1.69 (s, 3H) , 1.11 (t, 3H); (M + 1): 368.95 113. N '- (2,5-dimethyl-4 - ((methyl) (4- Ή-NMR (400 MHz, DMSO-d6) δ 7.68 (s,

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(pentafluoro-16sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide 1H), 7.57 (d, 2H), 6.85 (s, 1H), 6.73 (s, 1H), 6.45 (d, 2H), 3.40-3.24 (m, 2H), 3.19 (s, 3H), 2.96 (s, 3H), 2.12 (s, 3H), 1.96 (s, 3H), 1.12 (t, 3H); (M + 1): 422.2. 114. N '- (2-chloro-5- (methyl) -4 ((methyl) (4- (pentafluoro-16sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.70 (s, 1H), 7.57 (d, 2H), 7.13 (s, 1H), 6.94 (d, 1H), 6 , 45 (d, 2H), 3.43-3.30 (m, 2H), 3.17 (s, 3H), 2.94 (s, 3H), 1.95 (s, 3H), 1, 13 (t, 3H); (M + 1): 442.15 115. N '- (2-chloro-5- (methyl) -4 ((methyl) (3 (methylthio) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.08-7.03 (m, 2H), 6.92 (d, 1H), 6.54 (dd, 1H), 6.31 (t, 1H), 6.20 (dd, 1H), 3,323.26 (m, 2H), 3.12 (s, 3H), 2.96 (s, 3H), 2, 36 (s, 3H), 1.98 (s, 3H), 1.14 (t, 3H); (M + 1): 362.15 116. N '- (2,5-dimethyl-4 - ((2 ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.65 (s, 1H), 7.47 (dd, 1H), 7.39 (s, 1H), 7.21-7.15 (m, 1H), 6.84 (s, 1H), 6.64-6.60 (m, 2H), 6.33 (dd, 1H), 3.34-3.30 (m, 2H), 2.92 (s, 3H), 2.12 (s, 3H), 2.02 (s, 3H), 1.12 (t, 3H); (M + 1): 382.10 117. N '- (2-chloro-5-methyl-4 - (((2 ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.70 (s, 1H), 7.56 (s, 1H), 7.51 (dd, 1H), 7.30-7.26 (m, 1H), 7.04 (s, 1H), 6.92 (d, 1H), 6.73 (td, 1H), 6.37 (dd, 1H), 3.45-3.34 (m, 2H ), 2.96 (s, 3H), 2.04 (s, 3H), 1.14 (t, 3H); (M + 1): 402.15 118. N '- (4 - ((3- ((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.62-7.12 (m, 4H), 6.87 (s, 1H), 6.77-6.76 (m, 2H), 6, 70-6.65 (m, 2H), 3.34-3.40 (m, 2H), 2.92 (s, 3H), 2.11 (s, 3H), 2.06 (s, 3H) , 1.12 (t, 3H); (M + 1): 364.15 119. N '- (2,5-dimethyl-4 - ((4 (((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.91 (s, 1H), 7.62 (s, 1H), 7.37 (d, 2H), 6.89 (s, 1H), 6 , 67-6.62 (m, 3H), 3.48-3.33 (m, 2H), 2.92 (s, 3H), 2.11 (s, 3H), 2.07 (s, 3H ), 1.15 (t, 3H); (M + 1): 382.20 120. N '- (2-chloro-5- (methyl) -4 - ((4 ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 8.03 (s, 1H), 7.74-7.65 (m, 1H), 7.42 (d, 2H), 7.11 (s, 1H), 6.91 (s, 1H), 6.69 (d, 2H), 3.44-3.33 (m, 2H), 2.96 (s, 3H), 2.09 (s, 3H ), 1.13 (t, 3H);

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(M + 1): 402.10 121. N '- (2,5-dimethyl-4 - ((methyl) (2 ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.63-7.43 (m, 3H), 7.22 (dd, 1H), 7.02 (td, 1H), 6.66 (s, 1H ), 6.33 (s, 1H), 3.46-3.33 (m, 2H), 3.01 (s, 3H), 2.90 (s, 3H), 2.18 (s, 3H) , 1.98 (s, 3H), 1.10 (t, 3H); (M + 1): 396.40 122. N '- (2-chloro-5-methyl-4 (methyl (2 ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.68 (s, 1H), 7.54-7.49 (m, 2H), 7.27 (dd, 1H), 7.10 (td, 1H ), 6.88 (d, 1H), 6.55 (s, 1H), 3.38-3.32 (m, 2H), 3.02 (s, 3H), 2.94 (s, 3H) , 2.17 (s, 3H), 1.12 (t, 3H); (M + 1): 416.15 123. N '- (2,5-dimethyl-4 - ((methyl) (4 ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.67 (s, 1H), 7.39 (d, 2H), 6.85 (s, 1H), 6.72 (s, 1H), 6.48 (d, 2H), 3.34 - 3.26 (m, 2H), 3.16 (s, 3H), 2.93 (s, 3H), 2.12 (s, 3H), 1.95 (s, 3H), 1.12 (t, 3H); (M + 1): 396.40 124. N '- (2-chloro-5- (methyl) -4 ((methyl) (4 ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.43 (d, 2H), 7.15 (s, 1H), 6.96 (d, 1H), 6.51 (d, 2H), 3.46-3.33 (m, 2H ), 3.18 (s, 3H), 2.97 (s, 3H), 1.97 (s, 3H), 1.14 (t, 3H); (M + 1): 416.15 125. N '- (4 - ((3- ((difluoromethyl) thio) phenyl) ((methyl)) amino) -2,5-dimethylphenyl) -Netyl-N-methylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.67 (s, 1H), 7.40 (t, 1H), 7.17 (t, 1H), 6.84 (s, 1H), 6.78 (d, 1H), 6.71 (s, 1H), 6, 56 (s, 1H), 6.50 (d, 1H), 3.50-3.34 (m, 2H), 3.11 (s, 3H), 2.93 (s, 3H), 2.11 (s, 3H), 1.95 (s, 3H), 1.12 (t, 3H); (M + 1): 378.35 126. N '- (2,5-dimethyl-4 - ((3- ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.65 (d, 2H), 7.21 (t, 1H), 6.88-6.78 (m, 4H), 6.66 (s, 1H), 3.50-3.23 (m, 2H), 2.92 (s, 3H), 2.10 (s, 3H), 2.05 (s, 3H), 1.11 (t, 3H ); (M + 1): 382.30 127. N '- (2,5-dimethyl-4 - ((4- (methylthio) phenyl) amino) phenyl) -Netyl-N-methylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.59 (s, 1H), 7.26 (s, 1H), 7.10 (d, 2H), 6.85 (s, 1H), 6.62-6.59 (m, 3H), 3.48-3.33 (m, 2H), 2.91 (s, 3H), 2.34 (s, 3H), 2.07 (s, 6H), 1.11 (t, 3H); (M + 1): 328.30 128. N '- (2-chloro-5- (methyl) -4 - ((4 (methylthio) phenyl) amino) phenyl) -Netyl-N-methylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.65 (s, 1H), 7.39 (s, 1H), 7.14 (d, 2H), 7.04 (s, 1H), 6.84 (s, 1H), 6.69 (d, 2H), 3.41-3.34 (m, 2H), 2.94 (s, 3H), 2.37 (s, 3H), 2.09 (s, 3H), 1.12 (t, 3H); (M + 1): 348.10

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129. N '- (2,5-dimethyl-4 - ((methyl) (3 ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.68 (s, 1H), 7.25 (t, 1H), 6.85-6.81 (m, 2H), 6.72 (s, 1H), 6.61-6.55 (m, 2H), 3.34-3.3 l (m, 2H), 3.14 (s, 3H), 2.92 (s, 3H), 2, 12 (s, 3H), 1.94 (s, 3H), 1.12 (t, 3H); (M + 1): 396.40 130. N '- (2-chloro-5- (methyl) -4 ((methyl) (3 ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.28 (t, 1H), 7.14 (s, 1H), 6.96-6.93 (m, 2H), 6.68 (d, 1H), 6.63 (s, 1H), 3.46-3.33 (m, 2H), 3.17 (s, 3H), 2.97 (s, 3H ), 1.96 (s, 3H), 1.13 (t, 3H); (M + 1): 416.15 131. N '- (2,5-dimethyl-4 - ((methyl) (4 (methylthio) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.65 (s, 1H), 7.11 (d, 2H), 6.80 (s, 1H), 6.68 (s, 1H), 6 , 39 (d, 2H), 3.38-3.34 (m, 2H), 3.09 (s, 3H), 2.92 (s, 3H), 2.33 (s, 3H), 2, 10 (s, 3H), 1.95 (s, 3H), 1.12 (t, 3H); (M + 1): 342.25 132. N '- (2-chloro-5- (methyl) -4 ((methyl) (4 (methylthio) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 7.13 (d, 2H), 7.07 (s, 1H), 6.92 (s, 1H), 6 , 42 (d, 2H), 3.34-3.25 (m, 2H), 3.11 (s, 3H), 2.96 (s, 3H), 2.34 (s, 3H), 1, 98 (s, 3H), 1.14 (t, 3H); (M + 1): 362.15 133. N '- (2,5-dimethyl-4 - ((3- (pentafluoro-16sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.82 (s, 1H), 7.64 (s, 1H), 7.27 (t, 1H), 7.04-7.01 (m, 2H), 6.88 (s, 1H), 6.78-6.76 (m, 1H), 6.68 (s, 1H), 3.46-3.28 (m, 2H), 2.92 (s, 3H), 2.11 (s, 3H), 2.03 (s, 3H), 1.12 (t, 3H); (M + 1): 408.15 134. N '- (2-chloro-5- (methyl) -4 - ((3 (pentafluoro-16sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.95 (s, 1H), 7.69 (d, 1H), 7.33 (t, 1H), 7.10-7.07 (m, 3H), 6.91 (s, 1H), 6.84 (d, 1H), 3.46-3.43 (m, 2H), 2.95 (s, 3H), 2.08 (s, 3H ), 1.13 (t, 3H); (M + 1): 428.65 135. N '- (2,5-dimethyl-4 - ((methyl) (3 (pentafluoro-16sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.65 (s, 1H), 7.31 (t, 1H), 7.04 (dd, 1H), 6.87 (s, 1H), 6 , 73 (s, 2H), 6.67 (d, 1H), 3.35-3.33 (m, 2H), 3.17 (s, 3H), 2.92 (s, 3H), 2, 12 (s, 3H), 1.95 (s, 3H), 1.12 (t, 3H); (M + 1): 422.3 136. N '- (2-chloro-5- (methyl) -4 ((methyl) (3- (pentafluoro-16sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.74 (s, 1H), 7.34 (t, 1H), 7.18 (s, 1H), 7.10 (d, 1H), 6 , 97 (d, 1H), 6.75 (s, 1H), 6.69 (d, 1H), 3.46-3.40 (m, 2H), 3.20 (s, 3H), 2, 97 (s, 3H), 1.97 (s, 3H), 1.13-1.16 (m, 3H); (M + 1): 442.15 137. N '- (4 - ((3,5- ^X H-NMR (400 MHz, DMSO-d6) δ 8.27 (s,

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bis (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N methylformimidamide 1H), 7.67 (s, 1H), 7.12 (s, 1H), 7.00 (s, 2H), 6.91 (s, 1H), 6.72 (s, 1H), 3.34-3.30 (m, 2H), 2.92 (s, 3H), 2.12 (s, 3H), 2.04 (s, 3H), 1.12 (t, 3H); (M + 1): 418.35 138. N '- (4 - ((3,5bis (trifluoromethyl) phenyl) amino) -2-chloro-5-methylphenyl) -N-ethylN-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 8.38 (s, 1H), 7.72 (d, 1H), 7.20 (s, 1H), 7.17 (s, 1H), 7 , 05 (s, 2H), 6.96 (s, 1H), 3.45-3.34 (m, 2H), 2.96 (s, 3H), 2.07 (s, 3H), 1, 14 (t, 3H); (M + 1): 438.15 139. N '- (2-chloro-5- (methyl) -4 - ((3 ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.79 (s, 1H), 7.68 (d, 1H), 7.27 (t, 1H), 7.09 (s, 1H), 6 , 95 (d, 1H), 6.90-6.85 (m, 3H), 3.42-3.33 (m, 2H), 2.95 (s, 3H), 2.08 (s, 3H ), 1.13 (t, 3H); (M + 1): 402.15 140. N '- (2-chloro-4 - ((4- (dimethylamino) phenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.64 (s, 1H), 6.83-6.79 (m, 3H), 6.75-6.68 (m, 4H), 3, 48-3.23 (m, 2H), 2.89 (s, 3H), 2.79 (s 6H), 2.11 (s, 3H), 1.11 (t, 3H); (M + 1): 345.20 141. N '- (4 - ((4- (dimethylamino) phenyl) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.55 (s, 1H), 6.71 (d, 3H), 6.66-6.63 (m, 2H), 6.54 (d, 2H), 3.35-3.31 (m, 2H), 2.90 (s, 3H), 2.76 (s, 6H), 2.10 (s, 3H), 2.02 (s, 3H ), 1.10 (t, 3H); (M + 1): 325.25 142. N '- (2-chloro-4 - ((3 ((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.73-7.63 (m, 2H), 7.42 (t, 1H), 7.20 (t, 1H), 7.08 (s, 1H), 6.88-6.83 (m, 3H), 6.75 (dd, 1H), 3.423.33 (m, 2H), 2.98 (s, 3H), 2.09 (s, 3H ), 1.13 (t, 3H); (M + 1): 384.20 143. N '- (2-chloro-4 - ((3 ((difluoromethyl) thio) phenyl) ((methyl)) amino) -5-methylphenyl) -N-ethylN-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.41 (t, 1H), 7.20 (t, 1H), 7.12 (s, 1H), 6 , 94 (d, 1H), 6.83 (d, 1H), 6.58 (t, 1H), 6.54 (dd, 1H), 3.45-3.33 (m, 2H), 3, 14 (s, 3H) 3.00 (s, 3H), 1.97 (s, 3H), 1.14 (t, 3H); (M + 1): 398.95 144. N '- (4 - ((3- (difluoromethoxy) phenyl) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.62 (s, 1H), 7.51 (s, 1H), 7.27-6.90 (m, 2H), 6.87 (s, 1H), 6.65 (s, 1H), 6.45 (dd, 1H), 6.35 (dd, 1H), 6.31 (t, 1H), 3.35 (q, 2H), 2, 92 (s, 3H), 2.10 (s, 3H), 2.07 (s, 3H), 1.11 (t, 3H); (M + 1): 348.40 145. N '- (4 - ((3- ^X H-NMR (400 MHz, DMSO-d6) δ 7.67 (s,

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(difluoromethoxy) phenyl) ((methyl)) amino) -2,5-dimethylphenyl) -Netyl-N-methylformimidamide 1H), 7.30-6.93 (m, 2H), 6.83 (s, 1H), 6.70 (s, 1H), 6.37 (dd, 1H), 6.24 (dd, 1H), 6.14 (t, 1H), 3.34 (q, 2H), 3.13 (s, 3H), 2.93 (s, 3H), 2.11 (s, 3H), 1.96 (s, 3H), 1, 12 (t, 3H); (M + l): 362.50 146. N '- (2-chloro-4 - ((3 (difluoromethoxy) phenyl) amino) 5-methylphenyl) -N-ethyl-N methylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.69 (s, 2H), 7.30-6.93 (m, 3H), 6.87 (s, 1H), 6.52 (dd, 1H), 6.44 (dd, 1H), 6.39 (t, 1H), 3.423.34 (m, 2H), 2.95 (s, 3H), 2.09 (s, 3H), 1, 08 (t, 3H); (M + 1): 368.35 147. N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.59 (s, 1H), 7.24 (s, 1H), 7.15-6.77 (m, 4H), 6.646.60 (m, 3H), 3.35 (q, 2H), 2.91 (s, 3H), 2.11 (s, 3H), 2.02 (s, 3H), 1.15 (t, 3H); (M + 1): 348.40 148. N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.47 (s, 1H), 7.17-6.73 (m, 4H), 6.74-6.64 (m, 1H), 6, 47-6.35 (m, 2H), 3.52-3.31 (m, 2H), 3.05 (s, 3H), 2.81 (s, 3H), 2.14 (s, 3H) , 2.00 (s, 3H), 1.06 (t, 3H); (M + l): 362.50 149. N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.65 (s, 1H), 7.38 (s, 1H), 7.19-6.81 (m, 5H), 6.746.70 (m, 2H), 3.41-3.34 (m, 2H), 2.94 (s, 3H), 2.09 (s, 3H), 1.12 (t, 3H); (M + 1): 368.35 150. N '- (2-chloro-4 - ((4 (difluoromethoxy) phenyl) ((methyl)) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 7.16-6.79 (m, 5H), 6.47-6.43 (m, 2H), 3, 45-3.32 (m, 2H), 3.11 (s, 3H), 2.96 (s, 3H), 1.99 (s, 3H), 1.14 (t, 3H); (M + 1): 382.0 151. N '- (4 - ((2,5difluorophenyl) amino) -2,5dimethylphenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.64-7.51 (m, 1H), 7.40 (s, 1H), 7.12-7.05 (m, 1H), 6, 84 (s, 1H), 6.68 (s, 1H), 6.37-6.32 (m, 1H), 6.025.97 (m, 1H), 3.35-3.30 (m, 2H) , 2.92 (s, 3H), 2.11 (s, 3H), 2.04 (3, 3H), 1.12 (t, 3H); (M + 1): 318.3 152. N '- (2-chloro-4 - ((2,5difluorophenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.69 (s, 1H), 7.55 (s, 1H), 7.16-7.10 (m, 1H), 7.04 (s, 1H), 6.90 (s, 1H), 6.45 (tt, 1H), 6.18-6.14 (m, 1H), 3.44-3.33 (m, 2H), 2.95 (s, 3H), 2.07 (s, 3H), 1.13 (t, 3H); (M + 1): 338.15 153. N '- (4 - ((3,5- bis (trifluoromethyl) phenyl) ((methyl ¹ H-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.15 (s, 1H), 6.91 (s, 1H), 6.85 (s, 2H),

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)) amino) -2,5-dimethylphenyl) -Netyl-N-methylformimidamide 6.77 (s, 1H), 3.46-3.35 (m, 2H), 3.25 (s, 3H), 2.93 (s, 3H), 2.12 (s, 3H), 1.95 (s, 3H), 1.13 (t, 3H); (M + 1): 432.45 154. N '- (4 - ((3,5bis (trifluoromethyl) phenyl) ((methyl)) amino) -2-chloro-5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.76 (s, 1H), 7.24 (s, 1H), 7.21 (s, 1H), 7.00 (d, 1H), 6 , 87 (s, 2H), 3.41 (q, 2H), 3.27 (s, 3H), 2.98 (s, 3H), 1.98 (s, 3H), 1.15 (t, 3H); (M + 1): 452.20 155. N '- (2,5-dimethyl-4 - ((5- (methyl) 2 (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.63 (s, 1H), 7.30 (d, 1H), 6.83 (s, 1H), 6.77 (s, 1H), 6 , 66 (s, 1H), 6.51 (d, 1H), 6.14 (s, 1H), 3.36 (q, 2H), 2.90 (s, 3H), 2.07 (s, 3H), 2.10 (s, 3H), 1.96 (s, 3H), 1.09 (t, 3H); (M + 1): 364.4 156. N '- (4 - ((2,5difluorophenyl) ((methyl)) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.54 (s, 1H), 7.04-6.97 (m, 1H), 6.73 (s, 1H), 6.636.53 (m, 3H), 3.35-3.27 (m, 2H), 3.10 (s, 3H), 2.91 (s, 3H), 2.06 (s, 6H), 1.15 (t, 3H ); (M + 1): 332.15 157. N '- (2-chloro-4 - ((2,5difluorophenyl) ((methyl)) amino) - 5-methylphenyl) -N-ethyl-N - methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.68 (bs, 1H), 7.08-7.01 (m, 1H), 6.96 (s, 1H), 6.85 (d, 1H), 6.75-6.69 (m, 1H), 6.67-6.61 (m, 1H), 3.43-3.33 (m, 2H), 3.07 (s, 3H) , 2.95 (s, 3H), 2.08 (s, 3H), 1.13 (t, 3H); (M + 1): 352.7 158. N '- (2,5-dimethyl-4 - ((methyl) (5 (methyl) -2 (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.58 (s, 1H), 7.49 (d, 1H), 6.96 (d, 2H), 6.64 (s, 1H), 6 , 55 (s, 1H), 3.35-3.27 (m, 2H), 3.06 (s, 3H), 2.90 (s, 3H), 2.28 (s, 3H), 2, 06 (s, 3H), 1.97 (s, 3H), 1.10 (t, 3H); (M + 1): 378.2 159. N '- (4 - ((4-chloro-2 (trifluoromethyl) phenyl) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.65 (bs, 1H), 7.46 (d, 1H), 7.32 (dd, 1H), 7.19 (s, 1H), 6 , 86 (s, 1H), 6.70 (s, 1H), 6.32 (d, 1H), 3.353,30 (m, 2H), 2.92 (s, 3H), 2.12 (s, 3H), 1.98 (s, 3H), 1.12 (t, 3H); (M + 1): 384.6 160. N '- (2-chloro-4 - ((4-chloro-2 (trifluoromethyl) phenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.70 (s, 1H), 7.50 (d, 1H), 7.37 (dd, 1H), 7.32 (s, 1H), 7 .09 (s, 1H), 6.91 (d, 1H), 6.36 (d, 1H), 3.443.34 (m, 2H), 2.96 (s, 3H), 1.98 (s, 3H), 1.13 (t, 3H); (M + 1): 405.2 161. N '- (4 - ((4-chloro-2 (trifluoromethyl) phenyl) (methyl) amine) -2,5-dimethylphenyl) -N-ethyl- ^X H-NMR (400 MHz, DMSO-d6) δ 7.63-7.57 (m, 3H), 7.14 (d, 1H), 6.64 (s, 1H), 6.57 (s, 1H), 3.35-3.27 (m, 2H), 3.07 (s, 3H), 2.89 (s,

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N-methylformimidamide 3H), 2.05 (s, 3H), 1.97 (s, 3H), 1.11-1.07 (m, 3H) (M + 1): 398.2 162. N '- (2-chloro-4 - ((4-chloro-2 (trifluoromethyl) phenyl) ((methyl)) to mino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.59-7.70 (m, 3H), 7.26 (d, 1H), 6.82 (s, 2H), 3.42-3, 33 (m, 2H), 3.08 (s, 3H), 2.93 (s, 3H), 1.98 (s, 3H), 1.10-1.16 (m, 3H); (M + 1): 419 163. N '- (2-chloro-5- (methyl) -4 ((methyl) (2 (methylthio) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.63 (s, 1H), 7.18 (dd, 1H), 7.10 (td, 1H), 7.06 (td, 1H), 6 , 88 (s, 1H), 6.82 (dd, 1H), 6.74 (s, 1H), 3.30-3.28 (m, 2H), 2.98 (s, 3H), 2, 96 (s, 3H), 2.37 (s, 3H), 1.86 (s, 3H), 1.11 (t, 3H); (M + 1): 363.15 164. N '- (2-chloro-4 - ((3 (difluoromethoxy) phenyl) ((methyl)) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.13 (s, 1H), 7.10 (s, 1H), 6.94 (d, 1H), 6 , 42 (dd, 2H), 6.26 (dd, 1H), 6.18 (t, 1H), 3.45-3.34 (m, 2H), 3.13 (s, 3H), 2, 95 (s, 3H), 1.98 (s, 3H), 1.12 (t, 3H); (M + l): 383.00 165. N '- (2-chloro-5- (methyl) -4 - ((2 (methylthio) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.66 (s, 1H), 7.30 (dd, 1H), 7.07-7.03 (m, 1H), 6.90 (s, 1H), 6.85 (s, 1H), 6.81 (td, 1H), 6.77 (s, 1H), 6.49 (dd, 1H), 3.42-3.34 (m, 2H ), 2.94 (s, 3H), 2.38 (s, 3H), 2.05 (s, 3H), 1.13 (t, 3H); (M + 1): 349.10 166. N '- (4 - ((2-chloro-4 (trifluoromethyl) phenyl) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.68-7.62 (m, 3H), 7.34 (dd, 1H), 6.89 (s, 1H), 6.72 (s, 1H), 6.32 (d, 1H), 3.36 (q, 2H), 2.93 (s, 3H), 2.11 (s, 3H), 2.01 (s, 3H), 1, 11-1.16 (m, 3H); (M + 1): 384.55 167. N '- (2-chloro-4 - ((2-chloro-4 (trifluoromethyl) phenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.77-7.66 (m, 3H), 7.40-7.37 (m, 1H), 7.14 (s, 1H), 6, 95 (d, 1H), 6.35 (d, 1H), 3.46-3.35 (m, 2H), 2.97 (s, 3H), 2.02 (s, 3H), 1.14 (t, 3H); (M + 1): 404.15 168. N '- (4 - ((2-chloro-4 (trifluoromethyl) phenyl) ((methyl)) to mino) -2,5-dimethylphenyl) -N-ethylN-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.60-7.62 (m, 3H), 7.24 (d, 1H), 6.64 (s, 1H), 6.56 (s, 1H), 3.35 (q, 2H), 3.09 (s, 3H), 2.91 (s, 3H), 2.10 (s, 3H), 2.04 (s, 3H), 1, 11 (t, 3H); (M + 1): 398.60 169. N '- (2-chloro-4 - ((2-chloro-4 (trifluoromethyl) phenyl) ((methyl)) to mino) -5-methylphenyl) -N-ethyl-N- ^X H-NMR (400 MHz, DMSO-d6) δ 7.74-7.63 (m, 3H), 7.29 (d, 1H), 6.88 (s, 1H), 6.78 (s, 1H), 3.43-3.35 (m, 2H), 3.09 (s, 3H), 2.95 (s,

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methylformimidamide 3H), 2.10 (s, 3H), 1.11 - 1.14 (m, 3H); (M + 1): 418.20 170. N '- (2,5-dimethyl-4 - ((2- (methylthio) phenyl) amino) phenyl) -Netyl-N-methylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.61 (s, 1H), 7.30 (dd, 1H), 7.02-6.98 (m, 1H), 6.83 (s, 1H), 6.69-6.65 (m, 2H), 6.60 (s, 1H), 6.37 (dd, 1H), 3.35-3.29 (m, 2H), 2.92 (s, 3H), 2.38 (s, 3H), 2.12 (s, 3H), 2.01 (s, 3H), 1.12 (t, 3H); (M + 1): 328.45 171. N-ethyl-N '- (4 - ((4-fluoro-3- (1,1,2,2tetrafluoroethoxy) phenyl) amino) 2,5-dimethylphenyl) -Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.63 (s, 1H), 7.49 (s, 1H), 7.18-7.13 (m, 1H), 6,986.91 (m, 2H), 6.65 (s, 1H), 6.58-6.54 (m, 2H), 3.35-3.23 (m, 2H), 2.91 (s, 3H), 2.08 (s, 3H), 2.06 (s, 3H), 1.11 (t, 3H); (M + 1): 416.25 172. N '- (2-chloro-4 - ((4-fluoro-3- (1,1,2,2tetrafluoroethoxy) phenyl) amino) - 5-methylphenyl) -N-ethyl-N methylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.68 (d, 2H), 7.24-7.19 (m, 1H), 7.07 (s, 1H), 6.966.70 (m, 2H), 6.66-6.62 (m, 2H), 3.43-3.34 (m, 2H), 2.95 (s, 3H), 2.08 (s, 3H), 1.13 (t, 3H); (M + 1): 436.10 173. 5-chloro-N- (2-fluorophenyl) -N, 2dimethyl-4- ((morpholinomethylene) amino) aniline 1H-NMR (400 MHz, DMSO-d6) δ 7.63 (s, 1H), 7.21-7.16 (m, 1H), 6.93-6.66 (m, 3H), 6.38 (dt, 1H), 6.27 (dd, 1H), 3.39 (s, 2H), 3.12 (s, 3H), 2.92 (s, 3H), 2.11 (s, 3H), 1.97 (s, 3H), 1.14-1.07 (t, 3H); ( M + l): 430, l 174. N '- (2-chloro-4- (N- (2-fluorophenyl) methylsulfonamido) 5-methylphenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.74-7.65 (m, 3H), 7.42-7.36 (m, 1H), 7.35-7.29 (m, 1H ), 7.26-7.22 (m, 1H), 6.88 (d, 1H), 3,443.32 (m, 2H), 3.20 (d, 3H), 2.95 (s, 3H) , 2.29 (s, 3H), 1.12 (t, 3H); (M + 1): 398.15 175. N- (5-chloro-4 ((((ethyl (methyl) amino) methylene) to mino) -2-methyl-phenyl) -N- (2-fluorophenyl) acetamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.84-7.77 (m, 6H), 6.86-6.74 (m, 1H), 3.34-3.32 (m, 2H ), 2.95 (s, 3H), 2.13 (s, 3H), 1.98 (s, 3H), 1.16 (t, 3H); (M + 1): 362.20 176. N '- (2-chloro-4 - ((2 fluorophenyl) ((methyl)) amino) -5methylphenyl) -N, Ndimethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.67 (s, 1H), 7.03-7.01 (m, 2H), 6.94 (s, 1H), 6.876.82 (m, 2H), 6.82 (s, 1H), 3.07 (s, 3H), 3.00 (s, 3H), 2.92 (s, 3H), 2.01 (s, 3H); (M + l): 320.50 177. N '- (2-chloro-4- (ethyl (2fluorophenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.67 (s, 1H), 7.08-7.00 (m, 3H), 6.88-6.80 (m, 3H), 3, 52 (q, 2H), 3.37 (q, 2H), 2.94 (s, 3H), 1.98 (s, 3H), 1.14-1.07 (m, 6H); (M + 1): 348.10

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178. 5-chloro-N- (2-fluorophenyl) -N, 2dimethyl-4- ((morpholinomethylene) amino) aniline ¹ H-NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.08-7.01 (m, 2H), 6.96 (s, 1H), 6,926.79 (m, 2H), 5.74 (s, 1H), 3.63-3.60 (m, 4H), 3.54-3.50 (m, 4H), 3.07 (s, 3H), 2.02 (s, 3H); (M + 1): 362.10 179. 5-chloro-N- (2-fluorophenyl) -N, 2dimethyl-4 ((thiomorpholinomethylene) amino) aniline ^X H-NMR (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 7.08-7.03 (m, 2H), 6.95 (s, 1H), 6.936.87 (m, 3H), 3.84-3.80 (m, 2H), 3.64-3.60 (m, 2H), 3.07 (s, 3H), 2.62-2.60 (m, 4H) , 2.02 (s, 3H); (M + 1): 379.00 180. N-ethyl-N '- (5-fluoro-4 - ((4fluoro-3- (1,2,2,2tetrafluoroethoxy) phenyl) amino) 2-methylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.80 (s, 1H), 7.68 (d, 1H), 7.22-7.17 (m, 1H), 6,996.66 (m, 5H), 3.41-3.36 (m, 2H), 2.94 (s, 3H), 2.11 (s, 3H), 1.12 (t, 3H) (M + 1): 420, 50 181. N-ethyl-N '- (5-fluoro-4 - ((4fluoro-3- (1,2,2,2tetrafluoroethoxy) phenyl) ((methyl)) amino) -2-methylphenyl) -Nmethylformimidamide 1 H-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.22 (t, 1H), 7.05 (d, 1H), 6.95-6.67 (m, 2H), 6.53 (dt, 1H), 6.46 (q, 1H), 3.43-3.33 (m, 2H), 3.16 (s, 3H), 2.95 (s, 3H ), 2.13 (s, 3H), 1.16-1.08 (m, 3H); (M + 1): 434.1 182. N- (5-chloro-4- ((((ethyl ((methyl)) amino) methylene) amino) -2-methylphenyl) -N- (2chlorophenyl) acetamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.70 (s, 1H), 6.95-7.66 (m, 5H), 6.90 (s, 1H), 3.39 (q, 2H), 2.96 (s, 3H), 2.24 (s, 3H), 1.93 (s, 3H), 1.15 (t, 3H); (M + 1): 378.05 183. N '- (2-chloro-4- (N- (2-chlorophenyl) methylsulfonamido) 5-methylphenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.87 (dd, 1H), 7.65-7.76 (m, 2H), 7.54 (dd, 1H), 7.42 (td, 1H), 7.39-7.35 (m, 1H), 6.87 (d, 1H), 3.43-3.44 (m, 2H), 3.24 (s, 3H), 2.95 (s, 3H), 2.33 (s, 3H), 1.12 (t, 3H); (M + 1): 414.10 184. N '- (4 - ((4 ((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 7.62 (s, 1H), 7.36-7.08 (m, 3H), 6.88 (s, 1H), 6.66 (s, 1H), 6.63-6.59 (m, 2H), 3.36- 3.21 (m, 2H), 2.92 (s, 3H), 2.11 (s, 3H), 2.06 (s, 3H), 1.11 (t, 3H); (M + l): 364.50 185. N '- (2-chloro-4 - (((4 ((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.83 (s, 1H), 7.68 (d, 1H), 7.39-7.10 (m, 3H), 7.09 (s, 1H), 6.89-6.83 (m, 1H), 6.67 (d, 2H), 3.44-3.35 (m, 2H), 2.95 (s, 3H), 2.08 (s, 3H), 1.13 (t, 3H); (M + 1): 384.35 186. N '- (4 - ((4- ((difluoromethyl) thio) phenyl) ((methyl ^X H-NMR (400 MHz, DMSO-d6) δ 7.62 (s, 1H), 7.35-7.07 (m, 3H), 6.83 (s, 1H), 6.69 (d,

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l)) amino) -2,5-dimethylphenyl) -Netyl-N-methylformimidamide 1H), 6.48-6.43 (m, 2H), 3.40-3.38 (m, 2H), 3.18 (s, 3H), 2.99 (s, 3H), 2.15 (s, 3H), 2.01 (s, 3H), 1.16 (t, 3H); (M + 1): 378.55 187. N '- (2-chloro-4 - ((4 ((difluoromethyl) thio) phenyl) ((methyl)) amino) -5-methylphenyl) -N-ethylN-methylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.37-7.09 (m, 4H), 6.95 (d, 1H), 6,496.46 (m, 2H), 3.40-3.35 (m, 2H), 3.17 (s, 3H), 2.93 (s, 3H), 2.00 (s, 3H), 1.14 (t, 3H ); (M + 1): 399.0 188. N '- (2-chloro-4 (ethyl (phenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.12-7.06 (m, 2H), 7.05 (d, 1H), 6.93 (d, 1H), 6.59 (t, 1H), 6.42 (d, 2H), 3.56 (q, 2H), 3.45-3.34 (m, 2H), 2.96 (s, 3H ), 1.99 (s, 3H), 1.15 (m, 3H), 1.06 (t, 3H); (M + 1): 330.35 189. N- (5-chloro-4- (((ethyl ((methyl)) amino) methylene) amino) -2-methylphenyl) -Nphenylacetamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 7.38-7.16 (m, 6H), 6.92 (d, 1H), 3.39 (q, 2H), 2.95 (s, 3H), 2.10 (s, 3H), 1.88 (s, 3H), 1.13 (t, 3H); (M + 1): 344.15 190. N '- (2-chloro-4 - ((2- ((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.71 (s 1H), 7.49-7.09 (m, 5H), 6.93 (s, 1H), 6.75 (td, lH ), 6.43 (dd, 1H), 3.34-3.26 (m, 2H), 2.97 (s, 3H), 2.07 (s, 3H), 1.34 (t, 3H) ; (M + 1): 385.00 191. N '- (2-chloro-4 - ((2- ((difluoromethyl) thio) phenyl) ((methyl)) amino) -5-methylphenyl) -N-ethylN-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.66 (s, 1H), 7.53-7.23 (m, 3H), 7.13-7.07 (m, 2H), 6, 83 (d, 1H), 6.67 (s, 1H), 3.45-3.41 (m, 2H), 3.00 (s, 3H), 2.93 (s, 3H), 2.06 (s, 3H), 1.13 (t, 3H); (M + 1): 398.35 192. N '- (2-chloro-4- (ethyl (3methoxyphenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.87 (s, 1H), 7.10-6.77 (m, 3H), 6.28-6.20 (m, 1H), 6, 07-5.91 (m, 2H), 3.69 (s, 3H), 3.60-3.50 (m, 2H), 3.43-3.23 (m, 2H), 3.08 ( s, 3H), 1.76 (s, 3H), 1.35 (t, 3H), 0.98 (t, 3H); (M + 1): 361.45 193. N '- (2-chloro-4 - ((3 (difluoromethoxy) -4fluorophenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.96-7.52 (m, 2H), 7.39-6.77 (m, 4H), 6.63-6.53 (m, 2H ), 3.43-3.33 (m, 2H), 3.00 (s, 3H), 1.92 (s, 3H), 1.13 (t, 3H); (M + 1): 386.15 194. N '- (2-chloro-4- (N- (3- methoxyphenyl) methylsulfonamido) - 5-methylphenyl) -N-ethyl-N - ^X H-NMR (400 MHz, DMSO-d6) δ 7.79-7.61 (m, 2H), 7.29 (t, 1H), 6.94-6.81 (m, 4H), 3, 84-3.74 (m, 5H), 3.47 (s 3H), 2.98 (s, 3H),

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methylformimidamide 2.22 (s, 3H), 1.12 (t, 3H); (M + l): 411.00 195. N '- (4 - ((3- (difluoromethoxy) -4fluorophenyl) amino) -2,5dimethylphenyl) -N-ethyl-N methylformimidamide Ή-ΝΜΚ (400 MHz, DMSO-d6) 7.62 (s, 1H), 7.39 (d, 1H), 7.17-6.84 (m, 2H), 6.53 (dd, 1H), 6.60-6.36 (m, 2H), 6.46 (dd, 1H), 3,283.13 (m, 2H), 2.50 (s, 3H), 1.91 (s, 6H ), 1.62 (t, 3H); (M + 1): 366.55 196. N '- (2-chloro-4 - ((3 (difluoromethoxy) -4fluorophenyl) ((methyl)) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.79 (s, 1H), 7.34-7.12 (m, 1H), 7.18-7.12 (m, 2H), 6, 97 (d, 1H), 6.39-6.25 (m, 1H), 6.28-6.25 (m, 1H), 3.38-3.34 (m, 2H), 2.90 ( s, 3H), 2.50 (s, 6H), 1.14 (t, 3H); (M + 1): 401.00 197. N '- (4 - ((3- (difluoromethoxy) -4fluorophenyl) ((methyl)) amino) 2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.68 (s, 1H), 7.29-6.92 (m, 2H), 6.81 (s, 1H), 6.68 (s, 1H), 6.35-6.29 (m, 1H), 6.18 (dt, 1H), 3.523.30 (m, 2H), 3.12 (s, 3H), 2.90 (s, 3H ), 2.17 (s, 3H), 1.99 (s, 3H), 1.25 (t, 3H); (M + 1): 380.55 198. N '- (4 - ((2,5dimethylphenyl) amino) -2,5dimethylphenyl) -N-ethyl-N methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.62 (s, 1H), 6.90 (d, 1H), 6.70 (s, 1H), 6.63 (s, 1H), 6 , 41 (d, 1H), 6.34 (s, 1H), 6.12 (s, 1H), 3.36 (q, 2H), 2.92 (s, 3H), 2.07 (s, 3H), 2.12 (s, 6H), 2.01 (s, 3H), 1.11 (t, 3H) (M + 1): 310.45 199. N '- (2-chloro-4 - ((2,5dimethylphenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 6.97 (d, 1H), 6.83 (s, 1H), 6.76 (s, 1H), 6 , 55 (d, 2H), 6.28 (s, 1H), 3.41-3.36 (m, 2H), 2.94 (s, 3H), 2.10 (s, 3H), 2, 15 (s, 3H), 2.06 (s, 3H), 1.12 (t, 3H); (M + 1): 331.1 200. N- (5-chloro-4- (((ethyl ((methyl)) amino) methylene) amino) -2-methylphenyl) -N- (2chlorophenyl) propionamide Ή-ΝΜΚ (400 MHz, DMSO-d6) δ 7.69 (s, 1H), 7.57-5.31 (5H), 6.90 (s, 1H), 3.38 (q, 2H), 2.96 (s, 3H), 2.30-2.20 (m, 5H), 1.15 (t, 3H), 1.04 (t, 3H); (M + 1): 393.45 201. N-ethyl-N '- (5-fluoro-4 - ((4methoxyphenyl) amino) -2methylphenyl) -Nmethylformimidamide Ή-ΝΜΚ (400 MHz, DMSO-d6) δ 7.69-7.52 (m, 1H), 7.20 (s, 1H), 6.91-6.69 (m, 6H), 3.72 -3.50 (m, 2H), 3.42 (s, 3H), 2.92 (s, 3H), 2.25 (s, 3H), 1.11 (t, 3H); (M + 1): 316.55 202. N-ethyl-N '- (5-fluoro-4 - ((4methoxyphenyl) ((methyl)) amino) -2methylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.76 (s, 1H), 6.98-6.95 (m, 1H), 6.79-6.75 (m, 3H), 6, 60-6.57 (m, 2H), 3.67 (s, 3H), 3.39 (q, 2H), 3.12 (s, 3H), 2.96 (s, 3H), 2.13 (s, 3H), 1.20 (t, 3H); (M + l): 330.40 203. N- (5-chloro-4- Ή-ΝΜΚ (400 MHz, DMSO-d6) δ 7.64 (s,

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(((ethyl (methyl) amino) methylene) to mino) -2-methylphenyl) -N- (2 fluorophenyl) propionamide 1H), 7.57-7.04 (m, 5H), 7.00-6.57 (m, 1H), 3.35-3.29 (m, 2H), 3.04 (s, 3H) , 2.27-1.90 (m, 5H), 1.18 (t, 3H), 1.05 (t, 3H); (M + 1): 376.55 204. N '- (2-chloro-4- (N- (4-fluoro-3 (1,1,2,2tetrafluoroethoxy) phenyl) methylsulfonamido) -5-methylphenyl) -N-ethylN-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.78-7.67 (m, 2H), 7.52-7.45 (m, 2H), 7.41-7.37 (m, 1H ), 7.02-6.74 (m, 2H), 3.46-3.34 (m, 2H), 3.29 (s, 3H), 2.96 (s, 3H), 2.19 ( s, 3H), 1, ΙΟΙ, 15 (m, 3H); (M + 1): 514.95 205. N '- (2,5-dimethyl-4 - ((3- (1,2,2,2tetrafluoroethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) 7.61 (s, 1H), 7.17-6.39 (m, 8H), 3.36 (q, 2H), 2.93 (s, 3H ), 2.00 (s, 3H); 2.28 (s, 3H), 1.27 (t, 3H); (M + 1): 398.55 206. N '- (2,5-dimethyl-4 - ((methyl) (3 (1,1,2,2tetrafluoroethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.60 (s, 1H), 7.16 (t, 1H), 6.83 (t, 1H), 6.70 (d, 1H), 6 , 46 (d, 1H), 6.41-6.39 (m, 1H), 6.14 (s, 1H), 3.39-3.31 (m, 2H), 3.12 (s, 3H ), 2.90 (s, 3H), 2.11 (s, 3H), 1.97 (s, 3H), 1.12 (t, 3H); (M + 1): 412.1 207. N-ethyl-N '- (4 - ((2-fluoro-5methylphenyl) amino) -2,5dimethylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.62 (s, 1H), 6.96-6.91 (m, 2H), 6.79 (s, 1H), 6.64 (s, 1H), 6.42-6.39 (m, 1H), 6.21 (dd, 1H), 3.35 (q, 2H), 2.92 (s, 3H), 2.10-2.03 (m, 9H), 1.13-1.10 (m, 3H); (M + 1): 313.6 208. N-ethyl-N '- (5-fluoro-4 - ((2-fluorophenyl) amino) -2methylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.68 (s, 1H), 7.30 (s, 1H), 7.09 (d, 1H), 6.89-6.96 (m, 2H), 6.75-6.69 (m, 2H), 6.63 (t, 1H), 3.38 (q, 2H), 2.93 (s, 3H), 2.11 (s, 3H ), 1.12 (t, 3H); (M + 1): 304.5 209. N-ethyl-N '- (4 - ((2-fluoro-5methylphenyl) ((methyl)) amino) -2,5dimethylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.60 (s, 1H), 6.87 (dd, 1H), 6.71 (s, 1H), 6.64-6.59 (m, 3H), 3.39 (q, 2H), 3.04 (s, 3H), 2.90 (s, 3H), 2.19 (s, 3H), 2.06 (s, 3H), 2, 02 (s, 3H), 1.10 (t, 3H); (M + l): 328.60 210. N '- (2-chloro-4 - ((2-fluoro-5methylphenyl) ((methyl)) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.67 (s, 1H), 6.90-6.95 (m, 2H), 6.82 (s, 1H), 6.716.68 (m, 2H), 3.35-3.25 (m, 2H), 3.07 (s, 3H), 2.91 (s, 3H), 2.21 (s, 3H), 2.00 (s, 3H ), 1.10 (t, 3H); (M + 1): 349.05 211. N-ethyl-N '- (5-fluoro-2- (methyl) - 4- (phenylamino) phenyl) -N- ^X H-NMR (400 MHz, DMSO-d6) δ 7.73-7.68 (m, 2H), 7.15-6.99 (m, 3H), 6.77-6.66 (m,

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methylformimidamide 4H), 3.39-3.27 (m, 2H), 2.93 (s, 3H), 2.33 (s, 3H), 1.12-1.36 (m, 3H); (M + 1): 286.35 212. N '- (4 - ((2-chlorophenyl) amino) -5fluoro-2-methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.70 (s, 1H), 7.31 (dd, 1H), 7.09-7.05 (m, 2H), 6.98 (d, 1H), 6.78-6.72 (m, 2H), 6.52 (d, 1H), 3.43-3.34 (m, 2H), 2.95 (s, 3H), 2.14 (s, 3H), 1.13 (t, 3H); (M + 1): 320.1 213. N '- (4 - ((4- (tertbutyl) phenyl) amino) -5-fluoro-2methylphenyl) -N-ethyl-Nmethylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.37-6.71 (m, 7H), 3.49-3.28 (m, 2H), 2, 93 (s, 3H), 2.28 (s, 3H), 1.39 (s, 9H), 0.86 (t, 3H); (M + 1): 342.7 214. N-ethyl-N '- (5-fluoro-2- (methyl) - 4- (m-tolylamino) phenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.79 (s, 1H), 7.43-7.34 (m, 1H), 7.03-6.96 (m, 2H), 6, 74 (d, 1H), 6.55-6.49 (m, 3H), 3.43-3.30 (m, 2H), 2.95 (s, 3H), 2.03 (s, 3H) , 2.19 (s, 3H), 1.24 (t, 3H); (M + 1): 300.4 215. N- (5-chloro-4- (((ethyl ((methyl)) amino) methylene) amino) -2-methylphenyl) -Nphenylpropionamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.85 (s, 1H), 7.55-7.04 (m, 6H), 6.99-6.84 (m, 1H), 3, 40-3.19 (m, 2H), 3.07 (s, 3H), 2.30-1.88 (m, 5H), 1.18 (s, 3H), 1.04 (t, 3H) ; (M + 1): 358.25 216. N- (5-chloro-4 (((ethyl (methyl) amino) methylene) to mino) -2-methylphenyl) -N- (3methoxyphenyl) acetamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.81 (s, 1H), 7.51-7.08 (m, 2H), 7.12-6.69 (m, 4H), 3, 64 (s, 3H), 3.45-3.30 (m, 2H), 2.84 (s, 3H), 2.18 (s, 3H), 1.81 (s, 3H), 1. 08 (t, 3H); (M + 1): 375.05 217. N '- (2-chloro-4 - ((4-fluoro-3methoxyphenyl) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.78 (s, 1H), 7.32 (s, 1H), 7.12-6.91 (m, 2H), 6,886.74 (m, 1H), 6.59-6.51 (m, 1H), 6.26-6.11 (m, 1H), 3.76 (s, 3H), 3.54-3.27 (m, 2H) , 3.03 (s, 3H), 2.13 (s, 3H), 1.28 (t, 3H); (M + 1): 351.05 218. N-ethyl-N '- (4 - ((4-fluoro-3methoxyphenyl) amino) -2,5dimethylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.61 (s, 1H), 7.14 (s, 1H), 6.94-6.88 (m, 2H), 6.63 (s, 1H), 6.48 (dd, 1H), 6.10 (dt, 1H), 3.85 (s, 3H), 3.39-3.32 (m, 2H), 2.93 (s, 3H ), 2.18 (s, 3H), 2.00 (s, 3H), 1.11 (t, 3H); (M + 1): 330.55 219. N-ethyl-N '- (4 - ((4-fluoro-3methoxyphenyl) ((methyl)) amino) 2,5-dimethylphenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 6.97-6.91 (m, 1H), 6.85-6.66 (m, 1H), 6, 25-6.20 (m, 1H), 5.87-5.84 (m, 1H), 5.785.75 (m, 1H), 3.64 (s, 3H), 3.39-3.30 ( m, 2H),

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3.12 (s, 3H), 2.92 (s, 3H), 2.12 (s, 3H), 1.96 (s, 3H), 1.12 (t, 3H); (M + 1): 344.60 220. N '- (4 - ((2 ((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.64 (s, 1H), 7.84-6.47 (m, 5H), 6.70-6.54 (m, 2H), 6.39 (dd, 1H), 3.40-3.34 (m, 2H), 2.94 (s, 3H), 2.31 (s, 3H), 1.89 (s, 3H), 1 , 24 (t, 3H); (M + 1): 364.45 221. N '- (4 - ((2- ((difluoromethyl) thio) phenyl) ((methyl)) amino) -2,5-dimethylphenyl) -Netyl-N-methylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.63 (s, 1H), 7.42-7.27 (m, 2H), 7.13-6.97 (m, 3H), 6.62 (d, 1H), 6.45 (d, 1H), 3.34-3.29 (m, 2H), 3.00 (s, 3H), 2.93 (s, 3H), 2.22 (s, 3H), 1.96 (s, 3H), 1.10 (t, 3H); (M + l): 378.50 222. N '- (2-chloro-4 - ((4-fluoro-3methoxyphenyl) ((methyl)) amino) -5methylphenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 6.89-7.69 (m, 3H), 6.25 (dd, 1H), 5.88 (td, 1H ), 3.75 (s, 3H), 3.30-3.26 (m, 2H), 3.10 (s, 3H), 2.98 (s, 3H), 2.33 (s, 3H) , 1.13 (t, 3H); (M + 1): 365.05 223. N '- (2-bromo-6-fluoro-3 (methyl) -4- (phenylamino) phenyl) N-ethyl-N-methylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.62 (d, 2H), 7.14-7.11 (m, 2H), 6.95 (d, 1H), 6.716.67 (m, 3H ), 3.29-3.24 (m, 2H), 2.96 (s, 3H), 2.22 (s, 3H), 1.34 (t, 3H); (M + 1): 365.35 224. N '- (2-chloro-5- (methyl) -4 - ((5oxo-5,6,7,8tetrahydronaphthalene-2yl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 8.16 (s, 1H), 7.82-7.65 (m, 2H), 7.16-7.05 (m, 1H), 6.95 -6.87 (m, 1H), 6.59-6.51 (m, 1H), 6.406.20 (m, 1H), 3.48-3.28 (m, 2H), 3.06 (m , 3H), 2.80-2.73 (m, 2H), 2.48-2.42 (m, 2H), 2.13 (s, 3H), 1.98-1.91 (m, 2H ), 1.24-1.10 (t, 3H); (M + 1): 370.15 225. N '- (2-bromo-6-fluoro-3 (methyl) -4 ((methyl) (phenyl) amino) phenyl) -Netyl-N-methylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.74 (s, 1H), 7.31-7.04 (m, 3H), 6.70-6.66 (m, 1H), 6.48 (dd, 2H), 3.51-3.31 (m, 2H), 3.15 (s, 3H), 2.98 (s, 3H), 2.33 (s, 3H), 1 , 12 (t, 3H); (M + l): 379.50 226. N '- (2-chloro-5- (methyl) -4 - ((lmethylindoline-5yl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 7.69-7.49 (m, 1H), 6.81-6.69 (m, 3H), 6.67-6.59 (m, 2H) , 6.47-6.40 (m, 1H), 3.38-3.24 (m, 2H), 3.26-3.05 (m, 2H), 3.01-2.85 (m, 3H), 2,852.73 (m, 2H), 2.66 (s, 3H), 2.16 (s, 3H), 1.22 (t, 3H); (M + 1): 357.15 227. N '- (2,5-dimethyl-4 - ((5-oxo- 5,6,7,8-tetrahydronaphthalene-2- Ή-NMR (400 MHz, DMSO-d6) δ 8.07 (s, 1H), 7.63 (d, 2 H), 6.87 (s, 1H), 6.68 (s, 1H),

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yl) amino) phenyl) -N-ethyl-Nmethylformimidamide 6.48 (dd, 1H), 6.31 (d, 1H), 3.35-3.30 (m, 2H), 2.92 (s, 3H), 2.72 (t, 2H), 2.42-2.39 (m, 2H), 2.12 (m, 2H), 2.05 (s, 3H), 1.92 (s, 3H), 1.14 (t, 3H); (M + 1): 350.35 228. N-ethyl-N '- (5-fluoro-2- (methyl) - 4 - ((methyl) (phenyl) amino) phenyl) - N-methylformimidamide ¹ H-NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.16-7.00 (m, 3H), 6.80-6.56 (m, 4H), 3, 46-3.33 (m, 2H), 3.17 (s, 3H), 2.97 (s, 3H), 2.14 (s, 3H), 1.24-1.13 (m, 3H) ; (M + 1): 300.01 229. N '- (4 - ((4- (tertbutyl) phenyl) ((methyl)) amino) -5fluoro-2-methylphenyl) -N-ethyl-Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.70 (s, 1H), 7.16 (d, 3H), 6.98 (d, 2H), 6.75 (d, 1H), 6 , 51 (d, 1H), 3.46-3.35 (m, 2H), 3.10 (s, 3H), 2.92 (s, 3H), 2.15 (s, 3H), 1, 25 (s, 9H), 1.14 (t, 3H); (M + 1): 356.5 230. N-ethyl-N '- (5-fluoro-2- (methyl) 4 - ((methyl) (mtolyl) amino) phenyl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.03-6.99 (m, 2H), 6.78 (d, 1H), 6,516.37 (m, 3H), 3.34 (s, 3H), 3.15 (q, 2H), 2.94 (s, 3H), 2.50 (s, 3H), 1.98 (s, 3H), 1, 24-1.13 (m, 3H); (M + 1): 314.1 231. N-ethyl-N '- (7 - ((2methoxyphenyl) amino) -2,3-dihydro-1 H-indene-4-yl) -Nmethylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.65 (s, 1H), 6.90 (dd, 1H), 6.83-6.79 (m, 1H), 6.72 (td, 1H), 6.66 (td, 1H), 6.62-6.58 (m, 2H), 6.38 (s, 1H), 3.81 (2, 3H), 3.44-3.32 (m, 2H), 2.86 (s, 3H), 2.75-2.81 (m, 2H), 2.66 (t, 2H), 1.88-1.95 (m, 2H), 1.10 (t, 3H); (M + 1): 324.30 232. N-ethyl-N- (methyl) -N '- (7- (ptolylamino) -2,3-dihydro-1Hindene-4-yl) formimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.73-7.52 (m, 1H), 7.25-6.56 (m, 6H), 6.59 (dd, 1H), 3, 34 (q, 2H), 2.68-2.91 (m, 6H), 2.33-1.89 (m, 6H), 1.34-1.10 (m, 3H); (M + 1): 308.1 233. N '- (7 - ((4-chlorophenyl) amino) - 2,3-dihydro-1H-indene-4-yl) - N-ethyl-N-methylformimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 7.68-7.55 (m, 2H), 7.17-7.12 (m, 2H), 6.92-6.60 (m, 4H ), 3.34-3.42 (m, 2H), 2.92-2.67 (m, 5H), 2.52-2.50 (m, 2H), 2.08-1.89 (m , 2H), 1,340.80 (m, 3H); (M + 1): 328.15 234. N-ethyl-N- (methyl) -N '- (4 (phenylamino) naphthalene-1 yl) formimidamide ^X H-NMR (400 MHz, DMSO-d6) δ 8.39 (s, 1H), 7.97-7.80 (m, 3H), 7.44 (td, 2H), 7,266.63 (m, 7H), 3.58-3.22 (m, 2H), 3.07 (s, 3H), 1.40 (t, 3H); (M + 1): 304.55 235. N '- (2,5-dimethyl-4- (pyridine-2ylamino) phenyl) -N-ethyl-N- ^X H-NMR (400 MHz, DMSO-d6) δ 7.96 (s, 1H), 7.88 (s, 1H), 7.60-7.58 (m, 1H), 7.42-

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methylformimidamide 7.31 (m, 1H), 7.03 (s, 1H), 6.62 (s, 1H), 6.55 (d, 1H), 6.42 (d, 1H), 3.35-3 , 31 (m, 2H), 2.92 (s, 3H), 2.11 (s, 3H), 2.06 (s, 3H), 1.12 (t, 3H); (M + 1): 283.30 236. N '- (2,5-dimethyl-4 ((methyl) (pyridine-2yl) amino) phenyl) -N-ethyl-Nmethylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 8.08 (s, 1H), 7.73-7.47 (m, 1H), 7.33-7.28 (m, 1H), 6.87 (s, 1H), 6.71 (s, 1H), 6.52 (dd, 1H), 5.97 (d, 1H), 3.41-3.40 (m, 2H), 3.24 (s, 3H), 2.93 (s, 3H), 2.12 ( s, 3H), 1.95 (s, 3H), 1.12 (t, 3H); (M + 1): 297.40 237. N '- (2-chloro-5- (methyl) -4 (pyridine-2-ylamino) phenyl) -Netyl-N-methylformimidamide Ή-NMR (400 MHz, DMSO-d6) δ 8.03-8.02 (m, 2H), 7.65 (d, 1H), 7.50 (s, 1H), 7.49-7.45 (m, 1H), 6.82 (s, 1H), 6.64-6.61 (m, 2H), 3.42-3.34 (m, 2H), 2.94 (s, 3H), 2.12 (s, 3H), 1.13 (t, 3H); (M + 1): 303.30

* Names of compounds generated using Chemdraw Professional 16.0 [0174] Table 2 provides compounds of general formula (Ia)

Serial number Compound name Analytical data 238. Nl- (4-chlorophenyl) - 2,5-dimethylbenzene- 1,4-diamine (M + 1): 247 239. N '- (2-chloro-4 - ((2-fluorophenyl) (methyl) amine) -5-methylphenyl) -Nisopropylformimide Ή-NMR, DMSO-d6) δ 7.47 (s, 1H), 7.15 (s, 1H), 7.08-7.02 (m, 2H), 6.93-6.87 (m, 3H), 6.76 (s, 1H), 4.00-3.85 (m, 1H), 3.09 (s, 3H), 2.01 (s, 3H), 1.15 (d, 3H ), 1.22 (d, 3H); (M + l): 335.80

* Compound names generated using Chemdraw Professional 16.0

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116/154 [0175] The compounds of the present invention as defined by the general formula (I) and / or in Tables 1 and 2 can be prepared, in a known manner, in various ways, as described in Schemes 1-2.

Layout 1

[0176] The compound of formula la can be synthesized by treating compound 2 with triemethyl orthoformate in the presence of catalytic pTSA, followed by reaction with a secondary amine of the formula HNR2R3 as described in US 201130282.

[0177] Compound 1 is a critical intermediate where Y is a nitro group or protected amine functionality and can be synthesized by reacting the compound of formula 3

R ⁴

R ⁵ where X is a halogen and Y is a nitro group or an amine functionality protected with the corresponding aniline derivatives as mentioned in the European Journal of Organic Chemistry, 2016 (10), page No. 1908-1914; Green Chemistry, 2016, 16 (7), page No. 3494-3500; and Tetrahedron Letters, 2014, 55 (30), page 4098-4101.

Layout 2

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R ⁴ R ²

R ⁵

Buchwald Condition

R ⁴ R ²

R ⁸ R ⁵

1a [0178] The compound of formula la can also be synthesized by treating compound 4 with appropriately substituted anilines, using Buchwald conditions as mentioned in J. Med.Chem 2012, vol.55,19, page No. 8538-48; Synlett 2012, vol.23,13, page No. 2504-10; and Journal of Organic Chemistry, 2010, vol.75, 19, page No. 6477-88.

[0179] The compound of formula 4 can be synthesized by derivatives of the corresponding aniline and converting them to amidine using the methods of known literature.

[0180] The present invention is further illustrated by the following non-limiting examples. Structures of new compounds were confirmed by NMR and / or other appropriate analysis as indicated below.

EXAMPLE 1

Preparation of N '- [2,5-dimethyl-4- (phenyl amine) phenyl] -N-ethyl-Nmethylimidoformamide [0181] Step A: 2,5-dimethyl- / V-phenylbenzene-1,4-diamine

Tin (II) chloride (3.62 g, 16.097 mmol) was added. to a stirred solution of 4-anilino-2,5-dimethyl-nitrobenzene (1.3 g, 5.3365 mmol) in 1,4-dioxane and concentrated HCl (1: 1) (30 ml). The reaction mixture was heated to 100 ° C for 3-4 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and carefully basified with sodium bicarbonate at pH 7-8. The aqueous layer was extracted with 5% dichloromethane / methanol (3x100ml). The combined organic layer was washed with water (1 x 100 ml),

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118/154 brine solution (1x1 OOml). The organic layer was dried over anhydrous sodium sulfate. The organic layer was filtered and evaporated under high vacuum to obtain the residue, which was then purified by flash chromatography using 0-80% ethyl acetate: hexane as the eluent to give 2,5-dimethyl-N-phenylbenzene-

1,4-diamine (0.9 g) as a solid. LCMS (M + H) 249.75 [0182] Step B: N '- [2,5-dimethyl-4- (phenylamidine) phenyl] -N-ethyl-Nmethylimidoformamide

PTSA (0.02 g, 0.113 mmol) was added to a stirred solution of 4-anilino2, 5-dimethyl aniline (0.8 g, 3.791 mmol) in trimethyl orthoformate (80 ml), and the reaction mixture was heated to 100 ° C for 6 hours. After the complete disappearance of the amine, the reaction mixture was cooled and the volatiles evaporated. 1,4-dioxane (20 ml) was added to the residue followed by the addition of N-ethylmethyl amine (0.45 g, 7.582 mmol). The reaction mixture was heated to 100 ° C for 1-2 hours. After completion of the reaction, the volatiles were evaporated to obtain the residue which was then purified by flash chromatography eluting with 0-60% ethyl acetate: hexane as the eluent to give N '- [2,5-dimethyl-4 (phenylamino ) phenyl] -N-ethyl-N-methylimidoformamide (0.25 g) as a gum. Ή-NMR (400 MHz, DMSO-d6) δ 7.60 (bs, 1H), 7.17 (s, 1H), 7.08 (t, J = 7.8 Hz, 2H), 6.88 ( s, 1H), 6.64 (d, J = 7.3 Hz, 3H), 6.60 (t, J = 7.3 Hz, 1H), 3.51 3.35 (m, 2H), 3 , 02-2.84 (bs, 3H), 2.10 (s, 3H), 2.07 (s, 3H), 1.12 (t, J = 7.1 Hz, 3H)

EXAMPLE 2

Preparation of N '- {2,5-dimethyl-4- [methyl (phenyl) amine] phenyl} -N-ethyl-Nmethylimidoformamide [0183] Step A: Preparation of 4-N-methylaniline-2,5-dimethyl aniline

Tin (II) chloride (3.62 g, 16.097 mmol) was added. to a stirred solution of 4-N-methylaniline-2,5-dimethyl-nitrobenzene (2.0 g, 7.80 mmol) in

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1,4-dioxane and concentrated HCI (1: 1) (50 ml). The reaction mixture was heated to 100 ° C for 3-4 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and carefully basified with sodium bicarbonate at pH 7-8. The aqueous layer was extracted with 5% dichloromethane / methanol (3x100ml). The combined organic layer was washed with water (1x100ml), brine solution (1x100ml). The organic layer was dried over anhydrous sodium sulfate. The organic layer was filtered and evaporated under high vacuum to obtain the residue, which was then purified by flash chromatography using 080% ethyl acetate: hexane as the eluent to give 4-N-methylaniline-2,5dimethylaniline (1.5 g) as solid. LCMS (M + H) 227.40 [0184] Step B: Preparation of N '- {2,5-dimethyl-4- [methyl (phenyl) amine] phenyl} -N-ethyl-N-methylimidoformamide

PTSA (0.02 g, 0.099 mmol) was added to a stirred solution of 4-Nmethylanilino-2,5-dimethylaniline (0.7 g, 3.317 mmol) in trimethyl orthoformate (80 ml). The reaction mixture was heated at 100 ° C for 6 hours. After the reaction was completed, the reaction mixture was cooled and evaporated. To the residue was added 1,4-dioxane followed by the addition of N-ethylmethylamine (0.392 g, 6.635 mmol). The reaction mixture was heated at 100 ° C for 2 hours. Upon completion of the reaction, the volatiles were evaporated. The residue was purified by flash chromatography eluting with 0-60% ethyl acetate: hexane to obtain Ν '- {2,5-dimethyl-4- [methyl (phenyl) amino] phenyl} -N-ethyl-N-methylimidoformamide (0.25) as a gum. Ή-NMR (400 MHz, DMSO-d6) δ 7.73-7.51 (bs, 1H), 7.09 (t, J = 8.0 Hz, 2H), 6.82 (s, 1H), 6.69 (s, 1H), 6.61-6.54 (m, 1H), 6.42 (d, J = 7.8 Hz, 2H), 3.49-3.34 (m, 2H) , 3.11 (s, 3H), 2.93 (s, 3H), 2.12 (s, 3H), 1.97 (s, 3H), 1.13 (t, J = 7.1 Hz, 3H)

EXAMPLE 3

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Preparation of N '- [2-chloro-5-methyl-4- (phenylamino) phenyl] -N-ethyl-Nmethylimidoformamide [0185] Step A: Preparation of 4-anilino-2-chloro-5-methyl aniline

For a stirred solution of 4-anilino-2-chloro-5-methylnitrobenzene (2g, 7.61 mmol), iron (2.12 g, 3.80 mmol) and ammonium chloride (2.1 g, 3.80 mmol) in ethanol water (1: 1.50 ml)) the mixture was heated to 9 ° C for 2 hours. After the end of the reaction, the content was filtered through celite. The filtrate was concentrated and diluted with ethyl acetate (300 ml) and then washed with saturated sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to obtain the crude compound which was purified by flash column chromatography to obtain 4-anilino-2-chloro-5methyl aniline (1.6 g) as a gum. LCMS (M + H) 233.74 [0186] Step B: Preparation of N '- [2-chloro-5-methyl-4- (phenylamino) phenyl] N-ethyl-N-methylimidoformamide

PTSA (0.02 g, 0.1177 mmol) was added to a stirred solution of 4anilino-2-chloro-5-methylaniline (0.8 g, 3.791 mmol) in trimethyl orthoformate (80 ml), and the reaction mixture was heated to 100 ° C for 6 hours. Upon completion of the reaction, the reaction mixture was cooled and the volatiles evaporated.

1,4-dioxane was added to the residue followed by the addition of N-ethylmethylamine (0.45 g, 0.65 ml, 7.582 mmol). The reaction mixture was heated at 100 ° C for 2 hours. After completion of the reaction, the volatiles were evaporated under reduced pressure. The crude compound was purified by flash chromatography eluting with 0-60% ethyl acetate: hexane to give N '- [2-chloro-5-methyl-4 (phenylamino) phenyl] -N-ethyl-N-methylimidoformamide (0 , 25 g). ¹ H-NMR (400 MHz, DMSO-d6) δ 7.76-7.56 (br, 1H), 7.32 (s, 1H), 7.14 (t, J = 7.8 Hz, 2H) , 7.06 (s, 1H), 6.85 (s, 1H), 6.72 (d, J = 8.2 Hz, 2H), 6.68 (t, J = 7.3 Hz, 1H) , 3.42 (m, 2H), 3.04-2.85 (br, 3H), 2.11 (s, 3H), 1.13 (t, J = 6.9 Hz, 3H)

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EXAMPLE 4

Preparation of Ν '- {2-chloro-5-methyl-4- [methyl (phenyl) amino] phenyl} -N-ethyl-Nmethylimidoformamide [0187] Step A: Preparation of 5-chloro-N-2-dimethyl-N -phenylbenzene-1,4diamine

Iron (2.02 g, 36.17 mmol) and ammonium chloride (1.93 g, 36.17 mmol) in ethanol-water were added to a stirred solution of 5-chloro-N, 2-dimethyl-4- nitro-N-phenylaniline (2 g, 7.24 mmol) and the mixture (1: 1.50 ml) was heated to 90 ° C for 2 hours. After the end of the reaction, the content was filtered through celite. The filtrate was concentrated and diluted with ethyl acetate (300 ml) and then washed with saturated sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to obtain the crude compound which was purified by flash column chromatography to obtain

5-chloro-N-2-dimethyl-N-phenylbenzene-1,4-diamine (1.7 g) as a solid. LCMS (M + H) 227.32 [0188] Step B: Preparation of Ν '- {2-chloro-5-methyl-4- [methyl (phenyl) amino] phenyl} -N-ethyl-N-methylimidoformamide

PTSA (0.02 g, 0.11 mmol) was added to a stirred solution of 5-chloro-N2-dimethyl-N-phenylbenzene-1,4-diamine (0.9 g, 3.6 mmol) in trimethylortoformate ( 50 ml), and the reaction mixture was heated to 100 ° C for 6 hours. After completion of the reaction, the volatiles were evaporated. The residue was added

1,4-dioxane followed by the addition of N-ethylmethylamine (0.45 g, 0.65 ml, 7.582 mmol). The reaction was heated at 100 ° C for 2 hours. After completion of the reaction, the volatiles were evaporated and the residue was purified by flash chromatography eluting with 0-60% ethyl acetate: hexane to give N '- {2-chloro- 5-methyl-4 [methyl (phenyl) amino] phenyl} -N-ethyl-N-methylimidoformamide (0.8 g). ΉNMR (400 MHz, DMSO-d6) δ 7.79-7.63 (br, 1H), 7.13 (td, J = 7.0, 1.6 Hz, 2H), 7.08 (s, 1H ), 6.97-6.88 (br, 1H), 6.64 (t, J = 7.1 Hz, 1H), 6.46 (d, J = 7.7 Hz,

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2H), 3.51-3.36 (m, 2H), 3.13 (s, 3H), 3.05-2.91 (br, 3H), 1.99 (s, 3H), 1.15 (t, J = 6.9 Hz, 3H)

EXAMPLE 5

Preparation of N- [4 - ([ethyl (methyl) amino] methylidene} amino) -2,5-dimethylphenyl] N-phenylmethane ssulfonamide.

[0189] Step A was performed as described in the examples above.

[0190] Step B: Preparation of N- [4 - ([ethyl (methyl) amino] methylidene} amino) -2, 5-dimethylphenyl] -N-phenylmethanesulfonamide

P-Toluenesulfonic acid monohydrate (0.016 g, 0.086 mmol) was added to a stirred solution of (N- (4-amino-2,5-dimethylphenyl) -Nphenylmethanesulfonamide (0.5 g, 1.722 mmol) in trimethyl orthoformate (20.00 ml). The reaction mixture was stirred at 103 ° C for 3 hours. After 3 hours, the volatiles were evaporated and 1,4-dioxane (20 ml) was added to the residue under a nitrogen atmosphere. N-methylethylamine (1.018 g, 17.22 mmol) and stirred for 3 hours at 103 ° C. After completion of the reaction the volatiles were evaporated to obtain the crude compound which was then purified by flash column chromatography to obtain the desired N '- (2,5dimethyl-4- (N-phenylmethylsulfonamido) phenyl) -N-ethyl-N-methylformimidamide (0.294 g). ¹ H-NMR (400 MHz, DMSO-d6) δ 7,73- 7.53 (br, 1H), 7.35 (m, 4H), 7.28 (s, 1H), 7.23-7.14 (m, 1H), 6.69 (s, 1H), 3 , 49-3.36 (bs, 1H), 3.32-3.28 (bs, 1H), 3.24 (s, 3H), 3.02-2.87 (br, 3H), 2.19 (s, 3H), 2.16 (s, 3H), 1.12 (t, J = 7.1 Hz, 3H)

EXAMPLE 6

Preparation of N '- {4 - [(4-chlorophenyl) (methyl) amino] -2,5-dimethylphenyl} -N-ethyl-Nmethylimidoformamide

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123/154 [0191] Step A: Preparation of N-1- (4-chlorophenyl) -N'-1,2,5-trimethylbenzene-1,4-diamine

To a solution of N- (4-chlorophenyl) -N, 2,5-trimethyl-4-nitroaniline (0.6 g, 2.064 mmol) in ethanol (16 ml) and water (4.00 ml) was added chloride ammonium (0.442 g, 8.25 mmol) and iron (1.152 g, 20.64 mmol). The reaction mixture was stirred for 2 hours at 65 ° C. After completion of the reaction, it was cooled to room temperature and filtered through celite. The filtrate was evaporated to obtain residue which was placed in water and extracted with ethyl acetate. The ethyl acetate layer was washed with water (2x100 ml), brine (1x100 ml). The organic layer was collected and dried over anhydrous sodium sulfate. The organic layer was filtered, evaporated to obtain the residue, which was purified by flash chromatography to obtain the desired N1- (4-chlorophenyl) N1, 2,5-trimethylbenzene-1,4-diamine (0.5 g). LCMS (M + H) 261.77 [0192] Step B: Preparation of N '- {4 - [(4-chlorophenyl) (methyl) amino] -2,5dimethylphenyl} -N-ethyl-N-methylimidoformamide

To a stirred solution of Nl- (4-chlorophenyl) -N'-1,2,5-trimethylbenzene-1,4diamine (0.5 g, 1.917 mmol) in trimethyl orthoformate (20 ml) was added a monohydrate of p-toluenesulfonic acid (0.036 g, 0.192 mmol). The reaction mass was stirred at 105 ° C for 3 hours. Upon completion of the reaction, the volatiles were evaporated. Dioxane (20.00 ml) was added to the residue followed by Nmethylethanamine (1.133 g, 19.17 mmol) and the reaction mixture was stirred for 3 hours. Upon completion of the reaction, the volatiles were evaporated to obtain the crude product which was purified by preparative HPLC to obtain the desired N '(4 - ((4-chlorophenyl) (methyl) amino) -2, 5-dimethylphenyl) -N -ethyl-Nmethylformimidamide (0.35 g). Ή-ΝΜΚ (400 MHz, DMSO-d6) δ 7.71-7.55 (br, 1H), 7.12 (dd, J = 7.1, 2.1 Hz, 2H), 6.83 (s , 1H), 6.70 (s, 1H), 6.40 (dd, J = 6.9,

2.3 Hz, 2H), 3.48-3.34 (bs, 1H), 3.31-3.25 (bs, 1H), 3.11 (s, 3H), 3.02-2.86 (br, 3H), 2.12 (s, 3H), 1.95 (s, 3H), 1.13 (t, J = 7.1 Hz, 3H).

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EXAMPLE 7 [0193] Preparation of N '- {4 - [(3-chlorophenyl) (methyl) amino] -2,5dimethylphenyl} -N-ethyl-N-methylimidoformamide

Step A: Preparation of N-1- (3-chlorophenyl) -N'-1,2,5-trimethylbenzene-1,4diamine

To a solution of N- (3-chlorophenyl) -N, 2,5-trimethyl-4-nitroaniline (0.5 g, 1.720 mmol) in ethanol (15 ml) and water (3.00 ml) was added chloride ammonium (0.46g, 8.6mmol) and iron (0.960g, 17.20mmol). The reaction mixture was stirred for 2 hours at 65 ° C. After completion of the reaction, this mixture was cooled to room temperature and filtered through celite. The filtrate was evaporated to obtain the residue which was placed in water and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, evaporated to obtain the residue, which was purified by flash chromatography to obtain the desired N1- (3-chlorophenyl) -N1, 2,5-trimethylbenzene-1,4 -diamine (0.4 g). LCMS (M + H) 262.77 [0194] Step B: Preparation of N '- {4 - [(3-chlorophenyl) (methyl) amino] -2, 5dimethylphenyl} -N-ethyl-N-methylimidoformamide

To a stirred solution of Nl- (3-chlorophenyl) -N'-1,2,5-trimethylbenzene-1,4diamine (0.4 g, 1.534 mmol) in trimethyl orthoformate (16 ml) was added a monohydrate of p-toluenesulfonic acid (0.029 g, 0.153 mmol). The reaction mixture was stirred at 105 ° C for 3 hours. After completion of the reaction, the volatiles were evaporated. To the residue, dioxane (16.00 ml) was added followed by Nmethylethanamine (0.907 g, 15.34 mmol) and stirred at room temperature for 3 hours. Upon completion of the reaction, the volatiles were evaporated to obtain the crude compound which was then purified by flash column chromatography to obtain the desired N '- (4 - ((3-chlorophenyl) (methyl) amino) -2, 5- dimethylphenyl) -Netyl-N-methylformimidamide (0.23 g). ¹ H-NMR (400 MHz, DMSO-d6) δ 7.74 Petition 870190078277, of 8/13/2019, p. 130/187

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7.55 (br, 1H), 7.10 (t, J = 8.5 Hz, 1H), 6.84 (s, 1H), 6.72 (s, 1H), 6.60 (dot, J = 7.3, 1.1 Hz, 1H), 6.36 (m, 2H), 3.50-3.34 (m, 2H), 3.12 (s, 3H), 3.03-2, 87 (bs, 3H), 2.13 (s, 3H), 1.96 (s, 3H), 1.13 (t, J = 7.1 Hz, 3H)

EXAMPLE 8

Preparation of N '- {4 - [(3,4-dichlorophenyl) (methyl) amino] -2,5-dimethylphenyl} -N-ethylN-methylimidoformamide [0195] Step A: Preparation of Nl- (3, 4-dichlorophenyl ) -Nl, 2,5-trimethylbenzene-1,4-diamine

To a stirred solution of N- (3,4-dichlorophenyl) -N'-1,2,5-trimethyl-4-nitroaniline (0.6 g, 1.845 mmol) in ethanol (15 ml) and water (3.75 ml) ammonium chloride (0.395 g, 7.38 mmol) and iron (1.030 g, 18.45 mmol) were added. Then the reaction was stirred for 2 hours at 65 ° C. After completion of the reaction, the reaction mixture was filtered through celite. The filtrate was evaporated to obtain the residue, which was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried over anhydrous sodium sulfate and evaporated to obtain the residue which was purified by flash chromatography to obtain the desired N1- (3,4dichlorophenyl) -N'-1,2,5-trimethylbenzene -1.4-diamine (0.5 g). LCMS (M + H) 296.31 [0196] Step B: Preparation of Ν '- {4 - [(3,4-dichlorophenyl) (methyl) amino] -2,

5-dimethylphenyl} -N-ethyl-N-methylimidoformamide

To a stirred solution of Nl- (3,4-dichlorophenyl) -N'-1,2,5-trimethylbenzene-1,4diamine (0.5 g, 1.694 mmol) in trimethyl orthoformate (20 mL) was added a monohydrate of p-toluenesulfonic acid (0.016 g, 0.085 mmol). After stirring the reaction mixture at 105 ° C for 3 hours, the volatiles were evaporated and dioxane (20.00 ml) was added to the residue, followed by the addition of N-methylethylamine (1.001 g, 16.94 mmol). The reaction mixture was stirred at 103 ° C for 3 hours. After completion of the reaction, the volatiles and

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126/154 crude product was purified by column chromatography to obtain the desired N '- (4 - ((3,4-dichlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide (270 mg ). ¹ H-NMR (400 MHz, DMSO-d6) δ 7.77-7.52 (br, 1H), 7.29 (d, J = 9.2 Hz, 1H), 6.85 (s, 1H) , 6.73 (s, 1H), 6.55 (d, J = 2.3 Hz, 1H), 6.35 (dd, J = 9.2, 2.3 Hz, 1H), 3.52- 3.35 (m, 2H), 3.13 (s, 3H), 3.03-2.87 (bs, 3H), 2.12 (s, 3H), 1.96 (s, 3H), 1 , 13 (t, J = 6.9 Hz, 3H)

EXAMPLE 9

Preparation of Ν '- {2-chloro-5-methyl-4- [methyl (3, 4, 5-trifluorophenyl) amino] phenyl} N-ethyl-N-methylimidoformamide [0197] Step A: 5-chloro-N, 2-dimethyl-N- (3,4,5,5-trifluorophenyl) benzene-1,4-diamine

To a stirred solution of 5-chloro-N, 2-dimethyl-4-nitro-N- (3,4,5-trifluorophenyl) aniline (0.53 g, 1.603 mmol) in ethanol-water mixture was added iron (0.895 g, 16.03 mmol) and ammonium chloride (0.857 g, 16.03 mmol). The reaction mixture was heated to 90 ° C for 2 hours. After the reaction was completed, the reaction mixture was filtered through celite, concentrated and diluted with ethyl acetate (30 ml), washed with saturated sodium bicarbonate, the organic layer was separated, dried anhydrous sodium sulfate and concentrated to obtain the crude compound which was purified by flash chromatography to obtain 5 chloro-N1, 2-dimethyl-N 1- (3,4,5-trifluorophenyl) benzene-1,4-diamine (0.35 g) as a light brown gum. LCMS (M + H) 301.71 [0198] Step B: Preparation of Ν '- {2-chloro-5-methyl-4- [methyl (3, 4, 5trifluorophenyl) amino] phenyl} -N-ethyl-N-methylimidoformamide

To a stirred solution of 5-chloro-N1, 2-dimethyl-N'-1- (3,4,5-trifluorophenyl) benzene-1,4-diamine (0.3 g, 0.998 mmol) in trimethyl orthoformate ( 10 ml), a catalytic amount of ptoluenesulfonic acid monohydrate (0.019 g, 0.100 mmol) was added and the reaction content was heated to

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105 ° C under nitrogen atmosphere for 2 hours. After completion of the reaction, the volatiles were evaporated under high vacuum, the contents were diluted with

1,4-dioxane (8 ml), and N-ethylmethylamine (0.139 ml, 1.556 mmol) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours. Upon completion of the reaction, dioxane was evaporated under high vacuum and purified by flash column chromatography using 35-90% ethyl acetate: hexane to obtain N '- (2-chloro-5-methyl-4- (methyl) (3,4,5 -trifluorophenyl) amino) phenyl) -N-ethyl-N-methylformimidamide (0.299 g) as a gum. ΉNMR (400 MHz, DMSO-d6) δ 7.83-7.64 (br, 1H), 7.14 (s, 1H), 7.00-6.92 (br, 1H), 6.20 (dd , J = 12.0, 6.0 Hz, 2H), 3.49-3.34 (m, 2H), 3.13 (s, 3H), 3.05-2.92 (br, 3H), 1.99 (s, 3H), 1.15 (t, J = 6.9 Hz, 3H)

EXAMPLE 10

Preparation of N '- {2-chloro-5-methyl-4- [methyl (3-methylphenyl) -amino] phenyl} -N-ethylN-methylimidoformamide [0199] Step A: 5-chloro-N, 2-dimethyl- N- (3-methylphenyl) benzene-1,4-diamine

Iron (1.056 g, 18.92 mmol) and ammonium chloride (1.012 g, 18.92 mmol) in ethanol-water were added to a stirred solution of 5-chloro-N, 2-dimethyl-4-nitro-N ( m-tolyl) aniline (0.55 g, 1.892 mmol) and the mixture () was heated to 90 ° C for 2 hours. After the reaction was completed, the reaction mixture was filtered through celite, concentrated and diluted with ethyl acetate (30 ml), washed with saturated sodium bicarbonate, the organic layer was separated, dried anhydrous sodium sulfate and concentrated to obtain the residue which was purified by flash column chromatography to obtain 5-chloro-Nl, 2-dimethyl-Nl- (m-tolyl) benzene-1,4-diamine (0 , 34 g) as a light brown gum. LCMS (M + H) 261.77

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128/154 [0200] Step B: Preparation of N '- {2-chloro-5-methyl-4- [methyl (3-methylphenyl) amino] phenyl} -N-ethyl-N-methylimidoformamide

To a stirred solution of 5-chloro-Nl, 2-dimethyl-Nl- (m-tolyl) benzene-1,4diamine (0.34 g, 1.304 mmol) in trimethyl orthoformate (10 ml), a catalytic amount was added of ptoluenesulfonic acid monohydrate (0.025 g, 0.130 mmol) and the reaction content was heated to 105 ° C under a nitrogen atmosphere for 2 hours. After completion of the reaction, the volatiles were evaporated in vacuo, the residue was diluted with 1,4-dioxane (10 ml), and N-ethyl methylamine (0.181 ml, 2.086 mmol) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours. After the reaction was complete, dioxane was evaporated and the residue was purified by flash column chromatography using 35-90% ethyl acetate: hexane to obtain N '- (2-chloro-5-methyl-4 - (methyl (m-tolyl) amino) phenyl) -N-ethyl-Nmethylformimidamide (0.155 g) as gum. Ή-NMR (400 MHz, DMSO-d6) δ 7.83-7.61 (br, 1H), 7.07 (s, 1H), 7.02 (t, J = 8.0 Hz, 1H), 6.98-6.87 (br, 1H), 6.25 (dd, J = 8.0, 2.1 Hz, 1H), 6.08-5.94 (m, 2H), 3.65 ( s, 3H), 3.51-3.35 (m, 2H), 3.11 (s, 3H), 3.04-2.90 (br, 3H), 1.99 (s, 3H), 1 .15 (t, J = 6.9 Hz, 3H)

EXAMPLE 11

Preparation of N '- {2-chloro-4 - [(3,4-dichlorophenyl) (methyl) amino] -5-methylphenyl} -Netyl-N-methylimidoformamide [0201] Step A was carried out as described in the examples above. [0202] Step B: Preparation of N '- {2-chloro-4 - [(3,4-dichlorophenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimidoformamide

To a stirred solution of 5-chloro-N-l- (3,4-dichlorophenyl) -N-1,2-dimethylbenzene-

1,4-diamine (0.32 g, 1.014 mmol) in trimethyl orthoformate (10 ml), a catalytic amount of ptoluenesulfonic acid monohydrate (0.019 g, 0.101 mmol) was added and the reaction content was heated to

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105 ° C under nitrogen atmosphere for 2 hours. After completion of the reaction the contents were evaporated, the residue was diluted with 1,4-dioxane (10 ml), and N-ethyl methylamine (0.141 ml, 1.622 mmol) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours. After the reaction was complete, dioxane was evaporated and the residue was purified by flash column chromatography using 35-90% ethyl acetate: hexane to obtain N '- (2-chloro-4 - ((3 , 4-dichlorophenyl) (methyl) amino) -5-methylphenyl) -Netyl-N-methylformimidamide (0.302 g) as gum. ¹ H-NMR (400 MHz, DMSOd6) δ 7.83-7.64 (br, 1H), 7.32 (d, J = 9.2 Hz, 1H), 7.14 (s, 1H), 7 , 02-6.89 (br, 1H), 6.60 (d, J = 2.7 Hz, 1H), 6.36 (dd, J = 8.9, 3.0 Hz, 1H), 3, 50-3.34 (m, 2H), 3.14 (s, 3H), 3.05-2.89 (br, 3H), 1.98 (s, 3H), 1.15 (t, J = 6.9 Hz, 3H)

EXAMPLE 12 N '- {2-Chloro-4 - [(3-methoxyphenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-Nmethylimidoformamide [0203] Step A was carried out as described in the examples above. [0204] Step B: Preparation of N '- {2-chloro-4 - [(3methoxyphenyl) (methyl) amino] -5-methylphenyl] -N-ethyl-N-methylimidoformamide

To a stirred solution of 5-chloro-N-1- (3-methoxyphenyl) -N-1,2-dimethylbenzene-

1,4-diamine (0.3 g, 1.084 mmol) in trimethyl orthoformate (12 mL), a catalytic amount of ptoluenesulfonic acid monohydrate (0.021 g, 0.108 mmol) was added and the reaction content was heated to 105 ° C for 3 hours. After completion of the reaction, the volatiles were evaporated under high vacuum to obtain the residue which was taken up in 1,4-dioxane (12 ml). N-ethylmethylamine (0.151 ml, 1.734 mmol) was added and the contents were heated to 75 ° C for 4 hours. After the reaction was completed, the volatiles were evaporated and the residue was purified by flash column chromatography using 35-90% ethyl acetate: hexane to obtain N '- (2-chloro-4 - ((3-methoxyphenyl)

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130/154 (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimidamide (0.347 g) as gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.81-7.62 (br, 1H), 7.06 (s, 1H), 7.00 (t, J = 7.8 Hz, 1H) , 6.97-6.88 (br, 1H), 6.47 (d, J = 7.3 Hz, 1H), 6.29 (s, 1H), 6.25 (dd, 8.0, 2 , 0 Hz, 1H), 3.51-3.35 (m, 2H), 3.11 (s, 3H), 3.05-2.91 (br, 3H), 2.18 (s, 3H) , 1.98 (s, 3H), 1.15 (t, J = 7.1 Hz, 3H)

EXAMPLE 13

N '- (2-chloro-5-methyl-4- {methyl [4- (trifluoromethyl) phenyl] amino} phenyl) -N-ethyl-Nmethylimidoformamide [0205] Step A was carried out as described in the examples above. [0206] Step B: Preparation of N '- (2-chloro-5-methyl-4- {methyl [4 (trifluoromethyl) phenyl] amino} phenyl) -N-ethyl-N-methylimidoformamide

To a stirred solution of 5-chloro-Nl, 2-dimethyl-Nl- (4- (trifluoromethyl) phenyl) benzene-1,4-diamine (0.35 g, 1.112 mmol) in trimethyl orthoformate (10 ml), a catalytic amount of ptoluenesulfonic acid monohydrate (0.021 g, 0.111 mmol) was added and the reaction content was heated to 105 ° C under a nitrogen atmosphere for 2 hours. After the complete conversion of the starting material, the volatiles were evaporated and the residue was diluted with 1,4 dixane (10 ml). N-ethyl methylamine (0.155 ml, 1.779 mmol) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours. Upon completion of the reaction, dioxane was evaporated and the crude compound was purified by preparative HPLC to obtain N '- (2-chloro-5-methyl-4- (methyl (4 (trifluoromethyl) phenyl) amino) phenyl) -N- ethyl-N-methylformimidamide (0.359 g) as a pale yellow gum. Ή-NMR (400 MHz, DMSO-d6) δ 7.83-7.66 (br, 1H), 7.45 (d, J = 8.7 Hz, 2H), 7.16 (s, 1H), 7.03-6.92 (br, 1H), 6.55 (d, J = 8.7 Hz, 2H), 3.51-3.35 (m, 2H), 3.20 (s, 3H) , 3.05-2.90 (br, 3H), 1.98 (s, 3H), 1.16 (t, J = 6.9 Hz, 3H)

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EXAMPLE 14

Ν'- {2-chloro-5-methyl-4- [methyl (4-methylphenyl) amino] phenyl} -N-ethyl-N methylimidoformamide [0207] Step A was carried out as described in the examples above. [0208] Step B: Preparation of N '- {2-chloro-5-methyl-4- [methyl (4-methylphenyl) amino] phenyl} -N-ethyl-N-methylimidoformamide

To a stirred solution of 5-chloro-Nl, 2-dimethyl-Nl- (p-tolyl) benzene-1,4-diamine (0.35 g, 1.342 mmol) in trimethyl orthoformate (10 ml), a catalytic amount was added of ptoluenesulfonic acid monohydrate (0.026 g, 0.134 mmol) and the reaction content was heated to 105 ° C under a nitrogen atmosphere for 2 hours. After completion of the reaction, the volatiles were evaporated in vacuo, and the contents were diluted with 1,4dioxane (10 ml). N-ethylmethylamine (0.187 ml, 2.188 mmol) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours. Upon completion of the reaction, dioxane was evaporated to obtain the residue, which was purified by preparative HPLC to obtain N '- (2-chloro-5-methyl-4 (methyl (p-tolyl) amino) phenyl) -N- ethyl-N-methylformimidamide (0.317 g) as gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.82-7.62 (br, 1H), 7.05 (s, 1H), 6.94 (m, 3H), 6.38 (dd, J = 11.4, 2.7 Hz, 2H), 3.50-3.34 (m, 2H), 3.10 (s, 3H), 3.052.91 (br, 3H), 2.17 (s , 3H), 1.98 (s, 3H), 1.15 (t, J = 6.9 Hz, 3H)

EXAMPLE 15

Ν'- {2-Chloro-4- [(2-methoxyphenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-Nmethylimidoformamide [0209] Step A was carried out as described in the examples above. [0210] Step B: Preparation of N '- {2-chloro-4 - [(2methoxyphenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimidoformamide

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To a stirred solution of 5-chloro-Nl- (2-methoxyphenyl) -N-1,2-dimethylbenzene-

1,4-diamine (0.35 g, 1.255 mmol) in trimethyl orthoformate (10 ml), a catalytic amount of ptoluenesulfonic acid monohydrate (0.024 g, 0.126 mmol) was added and the reaction content was heated to 105 ° C under nitrogen atmosphere for 2 hours. Upon completion of the reaction, the volatiles were evaporated. The residue was diluted with 1,4-dioxane (10 ml). N-ethylmethylamine (0.176 ml, 2.023 mmol) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours. After completion of the reaction, dioxane was evaporated under high vacuum and the residue was purified by preparative HPLC to obtain N '- (2-chloro-4 - ((2methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl -N-methylformimidamide (0.310 g) as gum. Ή-NMR (400 MHz, DMSO-d6) δ 7.76-7.56 (br, 1H), 7.03-6.89 (m, 3H), 6.81 (m, 1H), 6.79 -6.72 (br, 1H), 6.73-6.61 (m, 1H), 3.70 (s, 3H), 3,473.34 (2H), 3.01 (s, 3H), 2, 99-2.88 (br, 3H), 1.84 (s, 3H), 1.12 (t, J = 7.1 Hz, 3H)

EXAMPLE 16

N - [5-chloro-4- ({- [ethyl (methyl) amino] methylidene} amino) -2-methylphenyl] -N phenylmethane sulfonamide [0211] Step A was carried out as described in the examples above. [0212] Step B: Preparation of N- [5-chloro-4 - ({[ethyl (methyl) amino] methylidene} amino) -2-methylphenyl] -N-phenihnethanesulfonamide

To a stirred solution of N- (4-amino-5-chloro-2-methylphenyl) -Nphenylmethanesulfonamide (0.32 g, 1.030 mmol) in trimethyl orthoformate (10 ml), a catalytic amount of ptoluenesulfonic acid monohydrate was added (0.020 g, 0.103 mmol) and the reaction content was heated to 105 ° C under nitrogen for 2 hours. After the complete conversion of the amine derivatives, the volatile compounds were evaporated under high vacuum to obtain the residue. 1,4-dioxane (10 mL) was added to this residue followed by

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133/154 by the addition of N-ethylmethylamine (0.233 ml, 2.68 mmol) at room temperature. The contents were heated to 75 ° C for 4 hours. Upon completion of the reaction, dioxane was evaporated under high vacuum and the residue was purified by preparative HPLC to obtain -N '- (2-chloro-5-methyl-4- (N-phenylmethylsulfonamido) phenyl) N-ethyl-N- methyl formimidamide (0.07 g) as gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.81-7.65 (br, 1H), 7.61 (s, 1H), 7.43-7.33 (m, 4H), 7, 23 (td, J = 5.6, 2.9 Hz, 1H), 6.95-6.87 (br, 1H), 3.54-3.34 (m, 2H), 3.27 (s, 3H), 3.03-2.91 (br, 3H), 2.20 (s, 3H), 1.14 (t, J = 6.9 Hz, 3H)

EXAMPLE 17

N '- {2-Chloro-4 - [(2-chlorophenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimidoformamide [0213] Step A was carried out as described in the examples above.

[0214] Step B: Preparation of -N '- {2-chloro-4 - [(2-chlorophenyl) (methyl) amino] 5-methylphenyl} -N-ethyl-N-methylimidoformamide

To a stirred solution of 5-chloro-Nl- (2-chlorophenyl) -Nl, 2-dimethylbenzene-1,4diamine (0.31 g, 1.102 mmol) in trimethyl orthoformate (10 ml), a catalytic amount of ptoluenesulfonic acid monohydrate (0.021 g, 0.110 mmol) and the reaction content was heated to 105 ° C under a nitrogen atmosphere for 2 hours. The volatile compounds were evaporated under high vacuum. The residue was diluted with 1,4-dioxane (10 ml). N-ethylmethylamine (0.192 ml, 2.205 mmol) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours. After the completion of the reaction, dioxane was evaporated under reduced pressure, the residue was purified by preparative HPLC to obtain -N '- (2-chloro-4 - ((2-chlorophenyl) (methyl) amino) -5-methylphenyl) -N -ethyl-N-methylformimidamide (0.359 g) as a pale yellow gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.80-7.59 (br, 1H), 7.40 (dd, J = 7.8, 1.4 Hz, 1H), 7.32- 7.23 (m, 1H), 7.11-6.99 (m, 2H),

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6.84 (s, 2H), 3.47-3.35 (m, 2H), 3.04 (s, 3H), 3.02-2.87 (br, 3H), 1.98 (s, 3H),

1.13 (t, J = 6.9 Hz, 3H)

EXAMPLE 18

Ν'- {2-chloro-4- [(4-chlorophenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-Nmethylimidoformamide [0215] Step A was carried out as described in the examples above. [0216] Step B: Preparation of N '- {2-chloro-4 - [(4-chlorophenyl) (methyl) amino] 5-methylphenyl} -N-ethyl-N-methylimidoformamide

To a stirred solution of 5-chloro-Nl- (4-chlorophenyl) -Nl, 2-dimethylbenzene-1,4diamine (0.32 g, 1.138 ml) in trimethyl orthoformate (10 ml), a catalytic amount of ptoluenesulfonic acid monohydrate (0.022 g, 0.114 mmoi) and the reaction content was heated to 105 ° C under a nitrogen atmosphere for 2 hours. After the complete conversion of the amine, the volatiles were removed in vacuo, the contents were diluted with 1,4 dixane (10 ml), and N-ethylmethylamine (0.198 ml, 2.276 ml) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours. Upon completion of the reaction, dioxane was removed and the residue was purified by preparative HPLC to obtain -N '- (2-chloro-4 - ((4-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl -N-methylformimidamide (0.360 g) as gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.86-7.64 (br, 1H), 7.16 (dd, J = 6.9,

2.3 Hz, 2H), 7.11 (s, 1H), 7.01-6.90 (br, 1H), 6.44 (dd, J = 6.9, 2.3 Hz, 2H), 3.51-3.34 (m, 2H), 3.13 (s, 3H), 3.04-2.92 (br, 3H), 1.98 (s, 3H), 1.15 (t, J = 6.9 Hz, 3H)

EXAMPLE 19

Ν'- {2-Chloro-4- [(4-methoxyphenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-Nmethylimidoformamide

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135/154 [0217] Step A was performed as described in the examples above. [0218] Step B: Preparation of N '- {2-chloro-4 - [(4methoxyphenyl) (methyl) amino] -5-methylphenyl] -N-ethyl-N-methylimidoformamide

To a stirred solution of 5-chloro-Nl- (4-methoxyphenyl) -N-1,2-dimethylbenzene-

1,4-diamine (0.3 g, 1.084 mmol) in trimethyl orthoformate (10 ml), a catalytic amount of ptoluenesulfonic acid monohydrate (0.021 g, 0.108 mmol) was added and the reaction content was heated to 105 ° C under nitrogen atmosphere for 2 hours. After completion of the reaction, the volatiles were evaporated under high vacuum. The residue was diluted with 1,4 dixane (10 ml). N-ethylmethylamine (0.188 ml, 2.188 mmol) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours, monitored by TLC. Upon completion of the reaction, dioxane was evaporated and the residue was purified by preparative HPLC to obtain N '- (2-chloro-4 - ((4methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N- methylformimidamide (0.079 g) as gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.82-7.62 (br, 1H), 7.03 (s, 1H), 6.96-6.85 (br, 1H), 6, 77 (dd, J = 6.9, 2.3 Hz, 2H), 6.46 (dd, J = 6.9, 2.3 Hz, 2H), 3.65 (s, 3H), 3.49 -3.35 (m, 2H), 3.08 (s, 3H), 3.04-2.92 (br, 3H), 1.99 (s, 3H), 1.15 (t, J = 6 , 9 Hz, 3H)

EXAMPLE 20

N '- (2-chloro-4 - ((4-methoxy-3-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide [0219] Step A was carried out as described in the examples above. [0220] Step B: Preparation of N '- (2-chloro-4 - ((4-methoxy-3methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimidamide

To a stirred solution of 5-chloro-Nl- (4-methoxy-3-methylphenyl) -Nl, 2dimethylbenzene-1,4-diamine (0.3 g, 1.032 mmol) in trimethyl orthoformate (10 ml), was added a catalytic amount of p-acid monohydrate

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136/154 toluenesulfonic (0.196 g, 1.032 mmol) and the reaction content was heated to 105 ° C under nitrogen for 2 hours. Upon completion of the reaction, the volatiles were evaporated to obtain the residue which was diluted with 1.4 dixane (10 ml). N-ethylmethylamine (0.090 ml, 1.032 mmol) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours. Upon completion of the reaction, dioxane was evaporated and the crude compound was purified by preparative HPLC to obtain N '- (2-chloro-4 - ((4-methoxy-3methylphenyl) (methyl) amino) -5-methylphenyl) -N -ethyl-N-methylformimidamide (0.124 g) as gum. Ή-NMR (400 MHz, DMSO-d6) δ 7.91-7.57 (br, 1H), 7.03 (s, 1H), 6.98-6.83 (br, 1H), 6.75 (d, J = 8.7 Hz, 1H), 6.37 (d, J = 2.7 Hz, 1H), 6.31 (dd, J = 8.7, 2.7 Hz, 1H), 3 , 68 (s, 3H), 3.51-3.37 (m, 2H), 3.07 (s, 3H), 3.05-2.90 (br, 3H), 2.05 (s, 3H ), 1.98 (s, 3H), 1.15 (t, J = 6.9 Hz, 3H)

EXAMPLE 21

N '- (2-chloro-4 - ((3,4-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide [0221] Step A was carried out as described in the examples above. [0222] Step B: Preparation of N '- (2-chloro-4 - ((3,4-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimidamide

To a stirred solution of 5-chloro-Nl- (3,4-dimethoxyphenyl) -Nl, 2-dimethylbenzene-1,4-diamine (0.24 g, 0.782 mmol) in trimethyl orthoformate (10 ml), an amount was added catalytic of ptoluenesulfonic acid monohydrate (0.015 g, 0.078 mmol) and the reaction content was heated to 105 ° C under nitrogen atmosphere for 2 hours. After completion of the reaction, the volatiles were evaporated under vacuum. The residue was diluted with 1,4-dioxane (10 ml). N-ethylmethylamine (0.122 ml, 1.408 mmol) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours. After completion of the reaction, dioxane was evaporated and the residue was purified by

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Preparative HPLC to obtain N '- (2-chloro-4 - ((3,4-dimethoxyphenyl) (methyl) amino) 5-methylphenyl) -N-ethyl-N-methylformimidamide (0.192 g) as gum. ΉNMR (400 MHz, DMSO-d6) δ 7.82-7.59 (br, 1H), 7.05 (s, 1H), 6.95-6.84 (br, 1H), 6.75 (d , J = 8.7 Hz, 1H), 6.19 (d, J = 2.7 Hz, 1H), 5.95 (dd, J = 8.7, 2.7 Hz, 1H), 3.64 (s, 3H), 3.63 (s, 3H), 3.50-3.34 (br, 2H), 3.10 (s, 3H), 3.04-2.88 (br, 3H), 1.99 (s, 3H), 1.14 (t, J = 6.9 Hz, 3H)

EXAMPLE 22

N '- (2-chloro-4 - ((3,5-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide [0223] Step A was carried out as described in the examples above. [0224] Step B: Preparation of N '- (2-chloro-4 - ((3,5-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimidamide

To a stirred solution of 5-chloro-Nl- (3,5-dimethoxyphenyl) -Nl, 2-dimethylbenzene-1,4-diamine (0.28 g, 0.913 mmol) in trimethyl orthoformate (10 ml), an amount was added catalytic of ptoluenesulfonic acid monohydrate (0.017 g, 0.091 mmol) and the reaction content was heated to 105 ° C under nitrogen atmosphere for 2 hours. After completion of the reaction, the volatiles were evaporated under vacuum. The residue was diluted with 1,4-dioxane (10 ml). N-ethylmethylamine (0.143 ml, 1.643 mmol) was added slowly at room temperature. The contents were heated to 75 ° C for 4 hours. Upon completion of the reaction, dioxane was evaporated and purified by preparative HPLC to obtain N '- (2-chloro-4 - ((3,5-dimethoxyphenyl) (methyl) amino) -5methylphenyl) -N-ethyl-N- methylformimidamide (0.267 g) as gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.83-7.61 (br, 1H), 7.06 (s, 1H), 6.96-6.86 (1H), 5.87 ( s, 1H), 5.58 (s, 2H), 3.63 (s, 6H), 3.51-3.34 (m, 2H), 3.10 (s, 3H), 3.04-2 , 87 (br, 3H), 1.99 (s, 3H), 1.14 (t, J = 6.6 Hz, 3H)

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EXAMPLE 23

N-ethyl-N '- (4 - ((3-methoxyphenyl) amino) -2, 5-dimethylphenyl) -N-methylformimidamide [0225] Step A was carried out as described in the examples above. [0226] Step B: Preparation of N-ethyl-N '- (4 - ((3-methoxyphenyl) amino) -2, 5dimethylphenyl) -N-methylformimidamide

To a stirred solution of Nl- (3-methoxyphenyl) 2,5-dimethylbenzene-1,4-diamine (0.22 g, 0.908 mmol) in trimethyl orthoformate (10 ml), a catalytic amount of acid monohydrate was added p-toluenesulfonic (0.017 g, 0.091 mmol) and the reaction content was heated to 105 ° C under a nitrogen atmosphere for 2 hours. After completion of the reaction, the volatiles were evaporated under vacuum. The residue was diluted with 1,4-dioxane (10 ml). Netylmethylamine (0.158 ml, 1.816 mmol) was added slowly at room temperature. The contents were heated to 90 ° C for 4 hours. After the reaction was completed, dioxane was evaporated and the crude compound was purified by preparative HPLC to obtain N-ethyl-N '- (4 - ((3-methoxyphenyl) amino) -2, 5-dimethylphenyl) - Nmethylformimidamide (0.235 g) as gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.70-7.49 (bs, 1H), 6.77 (s, 1H), 6.72 (d, J = 9.0 Hz, 2H) , 6.64 (s, 1H), 6.39 (d, J = 9.2 Hz, 2H), 3.63 (s, 3H), 3.54-3.19 (bs, 2H), 3, 05 (s, 3H), 2.91 (s, 3H), 2.09 (s, 3H), 1.96 (s, 3H), 1.11 (t, J = 7.1 Hz, 3H)

EXAMPLE 24

N-ethyl-N '- (4 - ((4-methoxyphenyl) (methyl) amino) -2, -5-dimethylphenyl) -Nmethylformimidamide [0227] Step A was carried out as described in the examples above.

[0228] Step B: Preparation of N-ethyl-N '- (4 - ((4-methoxyphenyl) (methyl) amino) 2,5-dimethylphenyl) -N-methylformimidamide

To a stirred solution of N-1- (4-methoxyphenyl) -N-1,2,5-trimethylbenzene-1,4-diamine (0.31 g, 1.209 mmol) in trimethyl orthoformate (10 ml), was

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139/154 a catalytic amount of ptoluenesulfonic acid monohydrate (0.023 g, 0.121 mmol) was added and the reaction content was heated to 105 ° C under a nitrogen atmosphere for 2 hours. After completion of the reaction, the volatiles were evaporated in vacuo, the contents were diluted with 1,4dioxane (10 ml), and N-ethylmethylamine (0.210 ml, 2.419 mmol) was added slowly at room temperature. The contents were heated to 90 ° C for 4 hours. Upon completion, dioxane was removed and the residue was purified by preparative HPLC using ammonium formate buffer to obtain N-ethyl-N '- (4 ((4-methoxyphenyl) (methyl) amino) -2,5- dimethylphenyl) -N-methylformimidamide (0.177 g) as a light yellow gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.70-7.49 (bs, 1H), 6.77 (s, 1H), 6.72 (d, J = 9.0 Hz, 2H) , 6.64 (s, 1H), 6.39 (d, J = 9.2 Hz, 2H), 3.63 (s, 3H), 3.54-3.19 (bs, 2H), 3, 05 (s, 3H), 2.91 (s, 3H), 2.09 (s, 3H), 1.96 (s, 3H), 1.11 (t, J = 7.1 Hz, 3H)

EXAMPLE 25

N '- (2-chloro-4 - ((2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide [0229] Step A: Preparation of N' - (4-Bromo-2-chloro-5 -methylphenyl) -N-ethylN-methylformimidamide

To a stirred solution of 4-bromo-2-chloro-5-methylaniline (2g, 9.07 mmol) in trimethyl orthoformate, a catalytic amount of p-toluenesulfonic acid monohydrate (0.173 g, 0.907 mmol) was added and heated the reaction content at 105 ° C under a nitrogen atmosphere for 2 hours. Upon completion of the reaction, the volatiles were removed in vacuo, the contents were diluted with 1,4-dioxane (15 ml), and N-ethyl methylamine (2,365 ml, 27.2 mmol) was added slowly at room temperature. The contents were heated to 90 ° C for 4 hours. After the reaction was completed, dioxane was removed and purified by flash column chromatography using ethyl acetate: hexane

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140/154 as an eluent to obtain N '- (4-bromo-2-chloro-5-methylphenyl) -N-ethyl-Nmethylformimidamide (2.2 g) as a light brown gum. LCMS (M + H) 289.60 [0230] Step B: N '- (2-chloro-4 - ((2-fluorophenyl) amino) -5-methylphenyl) -N-ethylN-methylformimidamide

In a stirred solution of N '- (4-bromo-2-chloro-5-methylphenyl) -N-ethyl-Nmethylformimidamide (0.521 g, 1.800 mmol), 2-fluoroaniline (0.2 g, 1.800 mmol), BINAP ( 0.112 g, 0.180 mmol), cesium carbonate (1.290 g, 3.96 mmol) was degassed in toluene for 15 minutes and palladium (II) acetate (0.061 g, 0.090 mmol) was added and further degassed for another 15 minutes and the contents were heated to 110 ° C for 8 hours. After completion of the reaction, the contents were filtered through celite, purified by flash column chromatography to obtain N '- (2-chloro-4 - ((2-fluorophenyl) amino) -5-methylphenyl) -Netyl-N-methylformimidamide ( 0.1318 g) as a gum. Ή-NMR (400 MHz, CHLOROFORM-D) δ 7.60-7.36 (br, 1H), 7.23 (s, 1H), 7.11-7.01 (m, 1H), 6.96 (t, J = 7.6 Hz, 1H), 6.73-6.85 (m, 3H), 5.38 (s, 1H), 3.68-3.22 (2H), 3.08 ( s, 3H), 2.19 (s, 3H), 1.25 (t, J = 7.2 Hz, 3H)

EXAMPLE 26

N '- (2-chloro-4 - ((3-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimidamide [0231] Step A was carried out as described in the examples.

[0232] Step B: N '- (2-chloro-4 - ((3-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide

To a stirred solution of 3 'chloroaniline (1 g, 7.84 mmol) of N' - (4-bromo-2 chloro-5-methylphenyl) -N-ethyl-N-methylformimidamide (2.270 g, 7.84 mmol), BINAP (0.488 g, 0.784 mmol), cesium carbonate (7.66 g, 23.52 mmol) was degassed in toluene for 15 minutes and palladium (II) acetate (0.264 g, 0.392 mmol) was added and further degassed during another 15 minutes and the

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141/154 content was heated to 110 ° C for 8 hours. After completion of the reaction, the contents were filtered through celite, purified by flash column chromatography to obtain N '- (2-chloro-4 - ((3-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide ( 0.8 g) as a gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.73 (bs, 1H), 7.66 (s, 1H), 7.10-7.14 (m, 1H), 7.07 (s, 1H), 6.88 (s, 1H), 6.706.63 (m, 1H), 6.58-6.60 (m, 2H), 3.50-3.33 (2H), 3.04-2 , 86 (3H), 2.08 (s, 3H),

1.13 (t, J = 7.0 Hz, 3H)

EXAMPLE 27

N '- (2-chloro-4 - ((3-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide [0233] Step A: Preparation of N' - (2-chloro-4- ((3-chlorophenyl) (methyl) amino) 5-methylphenyl) -N-ethyl-N-methylformimidamide (compound 53)

To a stirred solution of compound 52 of example 26 (0.3 g, 0.892 mmol), sodium hydride (0.043 g, 1.784 mmol) in DMF at 0 C was added, iodomethane (0.112 ml, 1.784 mmol) was added and stirred. up at room temperature for 2 hours. After the reaction was completed, the reaction mixture was poured onto crushed ice and diluted with ethyl acetate. The separated organic layer was washed with brine, dried over anhydrous sodium sulfate. Evaporated under high vacuum to obtain the residue, which was purified by preparative HPLC to obtain N '- (2-chlorophenyl) ((3-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl- Nmethylformimidamide (0.249 g) as a pale yellow gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.83-7.61 (1H), 7.10-7.14 (m, 2H), 6.95 (s, 1H), 6.63- 6.66 (m, 1H), 6.35-6.40 (m, 2H), 3.34-3.45 (m, 2H), 3.13 (s, 3H), 3.05-2, 87 (3H), 1.97 (s, 3H), 1.14 (t, J = 6.9 Hz, 3H)

EXAMPLE 28

N- (3-Chlorophenyl) -N, 2,5-trimethyl-4 - ((morpholinomethylene) amino) aniline

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142/154 [0234] Step A was performed as described in example 1.

[0235] Step B: Preparation of N- (3-chlorophenyl) -N, 2,5-trimethyl-4 ((morpholinethylene) amino) aniline

To a stirred solution of Nl- (3-chlorophenyl) -Nl, 2,5-trimethylbenzene-1,4diamine (0.3 g, 1.150 mmol) in trimethyl orthoformate, a catalytic amount of p-toluenesulfonic acid monohydrate was added (0.010 g, 0.053 mmol) and the reaction content was heated to 105 ° C under a nitrogen atmosphere for 2 hours. After completion of the reaction, the volatiles were evaporated under vacuum. The residue was diluted with 1,4-dioxane (10 ml), and morphine (0.200 ml, 2.301 mmol) was added slowly at room temperature. The contents were heated to 90 ° C for 4 hours. After the reaction was completed, dioxane was removed and purified by preparative HPLC to obtain N- (3-chlorophenyl) N, 2,5-trimethyl-4 - ((morpholinomethylene) amino) aniline (0.277 g) as a yellow gum pale. Ή-NMR (400 MHz, DMSO-d6) δ 7.69 (s, 1H), 7.07-7.11 (m, 1H), 6.85 (s, 1H), 6.75 (s, 1H ), 6.65-6.54 (1H), 6.34-6.36 (m, 2H), 3.61-3.63 (m, 4H), 3.59-3.38 (m, 4H ), 3.11 (s, 3H), 2.11 (s, 3H), 1.96 (s, 3H)

EXAMPLE 29

N- (3-chlorophenyl) -N, 2,5-trimethyl-4 - (((piperidine-1-ylmethylene) amino) aniline [0236] Step A was carried out as described in example 1.

[0237] Step B: N- (3-chlorophenyl) -N, 2,5-trimethyl-4 - ((piperidine-lylmethylene) amino) aniline

To a stirred solution of Nl- (3-chlorophenyl) -Nl, 2,5-trimethylbenzene-1,4diamine (0.3 g, 1.150 mmol) in trimethyl orthoformate, a catalytic amount of p-toluenesulfonic acid monohydrate was added (0.015 g,

(079 mmol) and the reaction content was heated to 105 ° C under nitrogen for 2 hours. After completion of the reaction, the volatiles were removed in vacuo, the contents were diluted with 1,4-dioxane (10 ml), and

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143/154 Piperidine (0.228 ml, 2.301 mmol) is added slowly at room temperature. The contents were heated to 90 ° C for 4 hours, monitored by TLC. Upon completion, dioxane was removed and purified by preparative HPLC using ammonium formate buffer to obtain N- (3-chlorophenyl) -N, 2,5-trimethyl-4 - (((piperidin-1-ylmethylene) amino) aniline (0.231 g) as white gum. Ή-NMR (400 MHz, DMSO-d6) δ 7.61 (s, 1H), 7.12-7.04 (m, 1H), 6.83 (s, 1H), 6.71 (s, 1H ), 6.58-6.60 (m, 1H), 6.34-6.36 (m, 2H), 3.64-3.33 (4H), 3.11 (s, 3H), 2, 11 (s, 3H), 1.95 (s, 3H), 1.59-1.62 (m, 2H), 1.48-1.54 (m, 4H)

EXAMPLE 30

N '- (4 - ((3-Chlorophenyl) (methyl) amino) -2, 5-dimethylphenyl) -N-cyanoformimidamide [0238] Step A was carried out as described in example 1.

[0239] Step B: N '- (4 - ((3-Chlorophenyl) (methyl) amino) -2, 5-dimethylphenyl) -Ncianoformimidamide

To a stirred solution of Nl- (3-chlorophenyl) -Nl, 2,5-trimethylbenzene-1,4diamine (0.3 g, 1.150 mmol) in trimethyl orthoformate, a catalytic amount of p-toluenesulfonic acid monohydrate was added (0.02 g, 0.105 mmol) and the reaction content was heated to 105 ° C under nitrogen for 2 hours. After completion of the reaction, the volatiles were removed in vacuo, and the contents were diluted with 1,4-dioxane (10 ml). Cyanamide (0.1 g, 2.379 mmol) was added slowly at room temperature. The contents were heated to 90 ° C for 4 hours. Upon completion of the reaction, dioxane was removed and purified by preparative HPLC using ammonium formate buffer to obtain N '- (4 - ((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -Ncianoformimidamide as a solid off-white (0.172 g). Ή-NMR (400 MHz, DMSO-d6) δ 11.09-10.13 (1H), 8.81-8.49 (1H), 7.38 (d, J = 41.7 Hz, 1H), 7.10-

7.14 (m, 1H), 7.05 (d, J = 13.8 Hz, 1H), 6.66 (d, J = 7.3 Hz, 1H), 6.46-6.39 (1H ), 6.39-6.31 (1H), 3.14 (3H), 2.19 (3H), 2.01 (s 3H)

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EXAMPLE 31

N-allyl-N '- (4 - ((3-chlorophenyl) (methyl) amino) -2, 5-dimethylphenyl) -Nmethylformimidamide [0240] Step A was carried out as described in example 1.

[0241] Step B: N-allyl-N '- (4 - ((3-chlorophenyl) (methyl) amino) -2, 5dimethylphenyl) -N-methylformimidamide

To a stirred solution of Nl- (3-chlorophenyl) -Nl, 2,5-trimethylbenzene-1,4diamine (0.3 g, 1.150 mmol) in trimethyl orthoformate, a catalytic amount of p-toluenesulfonic acid monohydrate was added (0.02 g, 0.105 mmol) and the reaction content was heated to 105 ° C under nitrogen for 2 hours. After the reaction was completed, the solvent was removed in vacuo and diluted with 1,4-dioxane (10 ml), and Nalylmethylamino (0.205 g, 2.88 mmol) was added slowly at room temperature. The contents were heated to 90 ° C for 4 hours. Upon completion, dioxane was removed and purified by preparative HPLC using ammonium formate buffer to obtain N-allyl-N '- (4 - ((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) - Nmethylformimidamide as a pale brown gum (0.227 g). Ή-NMR (400 MHz, DMSO-d6) δ 7.69 (s, 1H), 7.07-7.11 (m, 1H), 6.84 (s, 1H), 6.72 (s, 1H ), 6.58-6.61 (m, 1H), 6.35 (t, J = 2.3 Hz, 2H), 5.94-5.77 (1H), 5.18-5.23 ( m, 2H), 4.13-3.78 (2H), 3.11 (s, 3H), 2.90 (bs, 3H), 2.11 (s, 3H), 1.96 (s, 3H ).

[0242] As described in this document, the compounds of general formula (I) show an extremely high level of fungicidal activity that is exerted with respect to various phytopathogenic fungi that attack important agricultural crops. Compounds of the present invention have been evaluated for activity against one or more of the following:

Examples of biological tests (TESTE IN VITRO)

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145/154 [0243] Example 1: Pyricularia oryzae (Rice blast fungus): The compounds were dissolved in 0.3% DMSO and then added to a Potato Dextrose Agar vehicle just before being placed on Petri. 5 ml of the vehicle with compound was poured into sterile 60 mm petri dishes. After solidification, each plate was seeded with a 5 mm mycelial disk taken from the periphery of the virulent culture plate in active growth. The plates were incubated in growth chambers at 25 ° C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 11, 13, 16, 18, 20, 24, 25, 26, 27, 28, 29, 30, 31, 33, 34, 35 , 36, 38, 39, 40, 42, 43, 44, 45, 46, 47, 48, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63 , 64, 65, 66 67, 68, 69, 70,

71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91,

92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 110, 111, 112, 113, 115, 116, 117, 118, 119, 121, 122, 123, 125, 126, 129, 130,131,

133, 134, 135, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150,151,

152, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168,169,

170, 171, 172, 173, 176, 177, 178, 180, 181, 182, 184, 185, 186, 187, 188,189,

190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 205,206,

207, 208, 209, 210, 211, 212, 213, 214, 215, 217, 218, 219, 220, 221, 222,223,

224, 227, 228, 229 & 230 at 300ppm gave 70 to 100% control in these tests when compared to untreated reference samples that showed extensive disease development.

[0244] Example 2: Rhizoctonia solani (rice sheath rot / potato scab): The compounds were dissolved in 0.3% DMSO and then added to a Potato Dextrose Agar vehicle just before plating Petri. 5 ml of the vehicle with compound was poured into sterile 60 mm petri dishes. After solidification, each plate was

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146/154 seeded with a 5 mm mycelial disk taken from the periphery of the virulent culture plate in active growth. The plates were incubated in growth chambers at 25 ° C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 1, 2, 3, 4, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 18, 19, 20, 21, 24, 25, 26, 27, 29, 30, 31 , 33, 34, 35, 36, 38, 39,40, 42,

43, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 57, 58, 59, 60, 61, 62, 63, 64, 65,

66, 67, 68, 70, 71, 72, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88,

89, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107,

108, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123,124,

125, 126, 127, 128, 129, 130, 131, 132, 133, 135, 137, 139, 140, 142, 143,144,

145, 146, 147, 148, 149, 150, 151, 152, 153, 155, 156, 157, 158, 159, 160,161,

162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 173, 176, 177, 180, 181,184,

185, 186, 187, 188, 190, 191, 192, 195, 197, 198, 199, 201, 202, 205, 206,207,

208, 209, 210, 211, 212, 213, 214, 219, 220, 221, 222, 228, 229 & 230 at 300ppm gave 70 to 100% control in these tests when compared to untreated reference samples that showed extensive development disease.

[0245] Example 3: Botrytis cinerea (Gray rot): The compounds were dissolved in 0.3% DMSO and then added to a Potato Dextrose Agar vehicle just before being placed in Petri dishes. 5 ml of the vehicle with compound was poured into sterile 60 mm petri dishes. After solidification, each plate was seeded with a 5 mm mycelial disk taken from the periphery of the virulent culture plate in active growth. The plates were incubated in growth chambers at 22 ° C temperature and 90% relative humidity for seven days and radial growth was measured. Compounds 1, 2, 3, 4, 8, 9, 18, 19, 33, 34, 35, 38, 40, 46, 47, 48, 52, 53, 54, 55, 57, 58, 59, 60, 61 , 62, 63, 64, 70, 72, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 86, 87, 88, 89, 93, 94, 95, 97, 98, 99 , 100, 101, 103, 104, 105, 106, 107, 108, 110,

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115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 129, 130, 133, 135,

142, 143, 144, 145, 146, 148, 149, 150, 151, 152, 153, 155, 156, 157, 158, 159,

160, 161, 162, 166, 167, 168, 169, 173, 177, 181, 186, 187, 197, 199, 206, 207,

209, 210, 211, 212, 213, 214, 217, 218, 219, 220, 221, 223, 225, 229 & 230 a

300ppm gave 70 to 100% control in these tests when compared to untreated reference samples that showed extensive disease development.

[0246] Example 4: Alternaria solani (tomato / potato black spot): The compounds were dissolved in 0.3% DMSO and then added to a Potato Dextrose Agar vehicle just before being placed in Petri dishes . 5 ml of the vehicle with compound was poured into sterile 60 mm petri dishes. After solidification, each plate was seeded with a 5 mm mycelial disk taken from the periphery of the virulent culture plate in active growth. The plates were incubated in growth chambers at 25 ° C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 15, 16, 18,

19, 20, 21, 22, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40,

42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62,

63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83,

84, 85, 86, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 110, 112, 115, 116, 117, 118, 119, 121, 123, 125, 126, 127,

128, 129, 130, 131, 132, 133, 135, 137, 139, 140, 141, 142, 143, 144, 145, 146,

147, 148, 149, 150, 151, 152, 153, 155, 156, 157, 158, 159, 160, 161, 163, 164,

165, 166, 167, 168, 169, 170, 171, 173, 176, 177, 180, 181, 184, 185, 186, 187,

188, 189, 190, 191, 192, 193, 195, 196, 197, 198, 199, 200, 201, 202, 205, 206,

207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222,

223, 224, 225, 226, 227, 228, 229 & 230 at 300ppm gave 70 to 100%

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148/154 control in these tests when compared with untreated reference samples that showed extensive disease development.

[0247] Example 5: Colletotrichum capsici (anthracnose): The compounds were dissolved in 0.3% DMSO and then added to a Potato Dextrose Agar vehicle just before being placed in Petri dishes. 5 ml of the vehicle with compound was poured into sterile 60 mm petri dishes. After solidification, each plate was seeded with a 5 mm mycelial disk taken from the periphery of the virulent culture plate in active growth. The plates were incubated in growth chambers at 25 ° C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 2, 3, 4, 7, 8, 9, 11, 15, 18, 19, 24, 25, 26, 27, 29, 31, 32, 33, 34, 35,

36, 38, 39, 40, 43, 44, 46, 48, 51, 52, 53, 54, 55, 57, 58, 59, 60, 61, 62, 63.64,

66, 71, 72, 74, 75, 76, 77, 79, 80, 82, 83, 85, 86, 88, 89, 92, 93, 95, 96, 97.98,

99, 100, 102, 104, 106, 110, 111, 112, 113, 116, 117, 118, 119, 121, 123, 125,

126, 127, 129, 131, 133, 135, 141, 142, 144, 145, 146, 147, 148, 149, 151,152,

155, 156, 157, 158, 159, 160, 161, 162, 166, 167, 168, 169, 170, 171, 173,176,

180, 181, 184, 185, 186, 190, 191, 195, 197, 198, 199, 202, 205, 206, 207,209,

210, 211, 212, 213, 217, 218, 219, 220, 221, 222, 225 & 230 at 300ppm gave 100% control in these tests when compared to untreated reference samples that showed extensive disease development.

[0248] Example 6: Septoria lycopersici (Tomato leaf spot): The compounds were dissolved in 0.3% DMSO and then added to a Potato Dextrose Agar vehicle immediately before being placed in Petri dishes. 5 ml of the vehicle with compound was poured into sterile 60 mm petri dishes. After solidification, each plate was seeded with a 5 mm mycelial disc taken from the periphery of the virulent culture plate in

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149/154 active growth. The plates were incubated in growth chambers at 25 ° C temperature and 70% relative humidity for seven days and radial growth was measured. Compounds 1, 2, 3, 4, 6, 7, 8, 9, 11, 13, 15, 16, 18, 19, 20, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33 , 34, 35, 36, 37, 38, 39, 40, 43, 44, 45, 46, 47, 48, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62 , 63, 64.66, 72, 77, 86, 89, 98, 99, 102, 106, 110, 112, 116, 119, 123, 125, 126, 129, 135, 145, 148, 155, 166, 158 , 159, 160, 161, 166, 167, 168, 169, 171, 173, 180, 184, 186, 188, 190, 191, 194, 195, 197, 198, 199, 202, 205, 206, 207, 208 , 209, 211, 212, 213, 214, 217, 218, 219, 220, 221, 222, 223, 224, 225 & 230 at 300ppm gave 80 to 100% control in these tests when compared to untreated reference samples that showed extensive development of the disease.

[0249] Example 7: Fusarium culmorum Putrefaction of the stem of the cherry trees): The compounds were dissolved in 0.3% DMSO and then added to a Potato Dextrose Agar vehicle immediately before being placed in Petri dishes. 5 ml of the vehicle with compound was poured into sterile 60 mm petri dishes. After solidification, each plate was seeded with a 5 mm mycelial disk taken from the periphery of the virulent culture plate in active growth. The plates were incubated in growth chambers at 25 ° C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 1, 7, 8, 26, 27, 29, 31, 35, 38, 39, 40, 45, 52, 53, 54, 55, 57, 58, 59, 60, 61, 62, 64, 66, 71 , 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 89, 102, 104, 106, 116, 117, 119, 121, 123, 125, 126, 129, 145 , 147, 148, 151, 153, 155, 156, 158, 159, 160, 161, 166, 168, 170, 172, 181, 197, 205, 206, 209, 210, 213, 220 & 221 at 300ppm gave 70 to 100% control in these tests when compared to untreated reference samples that showed extensive disease development.

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Examples of biological tests (GREENHOUSE)

Example A: Pyricularia oryzae Test on Rice [0250] The compounds were dissolved in 2% DMSO / Acetone and then mixed with water to a calibrated spray volume of 50 ml. This 50 ml spray solution was poured into spray bottles for other applications.

[0251] To test the preventive activity of the compounds, young and healthy rice seedlings / plants, produced in the greenhouse, were sprayed with the preparation of the active compound at the indicated application rates, inside spray cabinets, using hollow cone nozzles. One day after treatment, the plants were inoculated with spore suspension (sterile water) containing inoculum of 1, 4 x ^{10 6} of Pyricularia oryzae. The inoculated plants were then kept in a greenhouse at 24 ° C and 95% relative humidity for the expression of the disease.

[0252] Visual assessment of the performance of the compound was carried out by classifying the severity of the disease (scale from 0 to 100%) in treated plants, at 3, 7, 10 and 15 days after application. The effectiveness (% of control) of the compounds was calculated by comparing the classification of the disease in the treatment with the untreated control. The sprayed plants were also evaluated for the phytotoxic effects of the compound, registering symptoms such as necrosis, chlorosis and dwarfism. Compounds 54, 58, 80, 129, 138 and 152 at 500 ppm gave 70-100% control in these tests when compared to the untreated control that showed extensive disease development. None of these compounds showed any phytotoxicity to rice culture.

Example B: Fusarium culmorum test on wheat [0253] The compounds were dissolved in 2% DMSO / Acetone and then mixed with water to a calibrated spray volume of 50

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151/154 ml. This 50 ml spray solution was poured into spray bottles for other applications. To test the preventive activity of the compounds, young and healthy wheat plants, produced in the greenhouse, were sprayed with the preparation of the active compound at the indicated application rates, inside spray cabinets, using hollow cone nozzles. One day after treatment, the plants were inoculated with spore suspension (2% malt) containing 2x10 ⁶ of Fusarium culmorum inoculum. The inoculated plants were then kept in a greenhouse at 24 ° C and temperature and 80-90% relative humidity for the expression of the disease.

[0254] Visual assessment of the performance of the compound was carried out by classifying the severity of the disease (scale from 0 to 100%) in treated plants, at 3, 7, 10 and 15 days after application. The effectiveness (% of control) of the compounds was calculated by comparing the classification of the disease in the treatment with the untreated control. The sprayed plants were also evaluated for the phytotoxic effects of the compound, registering symptoms such as necrosis, chlorosis and dwarfism. Compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 20, 21, 27, 28, 31, 35, 36, 82, 112, 139, 151, 152, and 158 to 500 ppm gave 70 -100% control in these tests when compared to the untreated control that showed extensive disease development. None of these compounds showed any phytotoxicity to wheat.

Example H: Botrytis cinera test on tomatoes [0255] The compounds were dissolved in 2% DMSO / Acetone and then mixed with water to a calibrated spray volume of 50 ml. This 50 ml spray solution was poured into spray bottles for other applications.

[0256] To test the preventive activity of the compounds, young and healthy beans / chili plants, produced in the greenhouse, were sprayed with the

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152/154 preparation of the active compound at the indicated application rates, inside spray cabinets, using hollow cone nozzles. One day after treatment, the plants were inoculated with spore suspension (2% malt) containing 1.2 χ 10 ⁶ of Botrytis cinera inoculum. The inoculated plants were then kept in an oven at 18-20 ° C temperature and 90-100% relative humidity for the expression of the disease.

[0257] Visual assessment of the performance of the compound was carried out by classifying the severity of the disease (scale from 0 to 100%) in treated plants, at 3, 7, 10 and 15 days after application. The effectiveness (% of control) of the compounds was calculated by comparing the classification of the disease in the treatment with the untreated control. The sprayed plants were also evaluated for the phytotoxic effects of the compound, registering symptoms such as necrosis, chlorosis and dwarfism. Compounds 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26 , 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 43, 44, 45, 46, 85, 86, 87, 88, 90, 96, 97, 99, 100, 102, 103, 123, 127, 128, 129, 133, 134, 135, 136, 137, 138, 150, 161, 162, 163, & 164 at 500ppm gave 70 to 100% control in these tests when compared to untreated reference samples. None of these compounds showed any phytotoxicity to the tomato crop.

Example D: Alternaria solani test on tomatoes [0258] The compounds were dissolved in 2% DMSO / Acetone and then mixed with water to a calibrated spray volume of 50 ml. This 50 ml spray solution was poured into spray bottles for other applications.

[0259] To test the preventive activity of the compounds, young and healthy tomato plants, produced in the greenhouse, were sprayed with the preparation of the active compound at the indicated application rates, within

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153/154 spray cabinets, using hollow cone nozzles. One day after treatment, the plants were inoculated with spore suspension (2% malt) containing 0.24 x 10 ⁶ of Alternaria solani inoculum. The inoculated plants were then kept in a greenhouse at 22-24 ° C in temperature and 90-95% relative humidity for the expression of the disease.

[0260] Visual assessment of the performance of the compound was carried out by classifying the severity of the disease (scale from 0 to 100%) in treated plants, at 3, 7, 10 and 15 days after application. The effectiveness (% of control) of the compounds was calculated by comparing the classification of the disease in the treatment with the untreated control. The sprayed plants were also evaluated for the phytotoxic effects of the compound, registering symptoms such as necrosis, chlorosis and dwarfism. Compounds 1, 2, 3, 5, 6, 8, 12, 13, 14, 15, 16, 17, 18, 19, 20, 22, 23, 24, 25, 26, 28, 29, 30, 31, 32 , 33, 35, 37, 40, 43, 44, 54, 66, 67, 75, 88, 89, 116, 117, 118, 119, 123, 124, 125, 129, 130, 131, 132, 139, 143 , 148, 156, 157 & 158 at 500ppm gave 70 -100% control in these tests when compared to untreated reference samples. None of these compounds showed any phytotoxicity to the tomato crop.

Example E: Corynespora corrica test on tomatoes [0261] The compounds were dissolved in 2% DMSO / Acetone and then mixed with water to a calibrated spray volume of 50 ml. This 50 ml spray solution was poured into spray bottles for other applications.

[0262] To test the preventive activity of the compounds, young and healthy tomato plants, produced in the greenhouse, were sprayed with the preparation of the active compound at the indicated application rates, inside spray cabinets, using hollow cone nozzles. One day after treatment, the plants were inoculated with spore suspension (aqueous Tween solution

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20) containing 2.6 x 10 ⁶ of Corynespora corrica inoculum. The inoculated plants were then kept in a greenhouse at 22-24 ° C in temperature and 90-95% relative humidity for the expression of the disease.

[0263] Visual assessment of the performance of the compound was carried out by classifying the severity of the disease (scale from 0 to 100%) in treated plants, at 3, 7, 10 and 15 days after application. The effectiveness (% of control) of the compounds was calculated by comparing the classification of the disease in the treatment with the untreated control. The sprayed plants were also evaluated for the phytotoxic effects of the compound, registering symptoms such as necrosis, chlorosis and dwarfism.

[0264] Compounds 1, 3, 13, 14, 15, 16, 17, 18, 19, 20 and 22 at 500 ppm gave 70 -100% control in these tests when compared to untreated. None of these compounds showed any phytotoxicity to the tomato crop.

[0265] Having described the invention with reference to certain preferred aspects, other aspects will become evident to those who are skilled in the art, starting from the consideration of the specification. It will be apparent to those skilled in the art that many modifications, both in materials and methods, can be practiced without departing from the scope of the invention.

Claims (26)

1. Compound, characterized by the fact that it is of general formula (I) Rl R ⁵ (D where R ¹ is selected from the group consisting of hydrogen, CN, SR, S (O) _n R, OR, C1-12-alkyl, C1-12-alkoxy, C1-12-alkylthio, C2-i2-alkenyl, C2-i2 -alkynyl, C1-12-haloalkyl, C2-i2-haloalkenyl, C2-i2-haloalkynyl, Cs-s-cycloalkyl, C48-cycloalkenyl, Cs-s-cycloalkynyl; where, in the cyclic ring system, one or more carbon atoms can be replaced by hetero atoms selected from the groups consisting of N, O, and S (O) _n ; R ² and R ³ are independently selected from the group consisting of hydrogen, CN, S (O) _n R, OR ', (C = O) -R, C1-12-alkyl, C2-i2-alkenyl, C2-12alkynyl, C1-12-haloalkyl, C2-i2-haloalkenyl, C2-i2-haloalkynyl, C3-8cycloalkyl, C4-8-cycloalkenyl, Cs-s-cycloalkyl, Cs-is-aryl, Cy-iç-aralkyl, Cj-iç- alkaryl; where, in the cyclic ring system, one or more carbon atoms can be replaced by hetero atoms selected from the groups consisting of N, O, and S (O) _n ; R ¹ and R ² , R ² and R ³ or R ¹ and R ³ together with the atoms to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) _m and SiR'2 can form a ring of four to seven members, which in turn can be Petition 870190078277, of 8/13/2019, p. 161/187 2/26 replaced by one or more X, R ', OR', SR ', NR'2, SiR'3, COOR', CN, and CONR'2; and where all groups of R ¹ , R ² , and R ³ can be optionally substituted by one or more groups selected from the group consisting of X, R ', OR', SR ', NR' ₂ , SiR ' ₃ , COOR ', CN, and CONR'₂; R ⁴ , R ⁵ , R ⁶ and R ⁷ are independently selected from the group consisting of hydrogen, X, CN, SCN, SF ₅ , S (O) _n R, SiR ' ₃ , OR, NR'R, (C = O ) -R, -NR COR, Ci_i2-alkyl, C2-i2-alkenyl, C2-i2-alkynyl, Ci_i2-haloalkyl, C2-12haloalcenilo, C2-I2 haloalkynyl, Ci_i2-haloalkoxy, Ci_i2-haloalkylthio, _C3 _8cicloalquilo, C4-8-cycloalkyl, Cs-s-cicloalquinil, _C3 _8-cycloalkyloxy, _C3 _8cicloalquiltio, Cs-is-aryl, aralkyl IC-Cy-Cy-IC-alkaryl; where, in the cyclic ring system, one or more carbon atoms can be replaced by hetero atoms selected from the groups consisting of N, O, and S (O) _n ; and all the groups mentioned above can be optionally substituted by one or more groups selected from the group consisting of X, R ', OR', SR ', NR' ₂ , SíR ' ₃ , COOR', CN, and CONR '₂; or where R ⁴ and R ⁷ or R ⁵ and R ⁶ together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) m and SiR'2 can form a four to seven membered ring, which in turn can be replaced by one or more X, R ', OR', SR ', NR'2, SiR'3, COOR', CN, and CONR'2; and where all groups of R ⁴ , R ⁵ , R ⁶ and R ⁷ can be optionally substituted by one or more groups selected from the group consisting of X, R ', OR', SR ', NR'2, SiR'3 , COOR ', CN, and CONR'₂; R ⁸ is selected from the group consisting of hydrogen, CN, SCN, S (O) _n R, SiR ' ₃ , NR'R, (C = O) -R, CR-NR, Ci_i ₂ -alkyl, C ₂ .i2 alkenyl, C2-12alquinil, Ci_i2-haloalkyl, C2-i2 haloalkenyl, C2-I2 haloalkynyl, C ₃ _8cicloalquilo, C4-8-cycloalkenyl, Cs-s-cicloalquinil, Cs-is-aryl, Cy-IC-aralkyl , Petition 870190078277, of 8/13/2019, p. 162/187 3/26 -C Ic-alkaryl, heterocyclic, _C3 _8-alkyl-heterocyclyl; where, in the cyclic ring system, one or more carbon atoms can be replaced by hetero atoms selected from the groups consisting of N, O, and S (O) _n ; and all of the groups mentioned above may be replaced by one or more groups selected from the group consisting of X, R ', OR', SR ', NR'2, SiR' ₃ , COOR ', CN, and CONR'₂; or where A is selected from the group consisting of fused or unfused C-is-aryl, Cs-is-heteroaryl, where one or more carbon atoms are replaced by heteroatoms selected from N, O, S and optionally including 1 to 3 members in rings selected from the group consisting of C (= O), C (= S), S (O) _m and SiR'2, optionally substituted by one or more groups of R ⁹ ; Where R ⁹ is selected from the group consisting of hydrogen, X, CN, SCN, SF5, R, OR, NO2, NR ₂ , SíR ' ₃ , (C = O) -R, S (O) _n R, OS (O) _n R, OSiR ' ₃ , NR'S (O) _n R, Ci_ ₈ -alkyl-S (O) _n R, Ci_ ₈ -alkyl- (C = O) -R, CR' = NR, S (O) _n C5 -i8-aryl, S (O) _n-C7-i9 aralkyl, -S (O) _n-C7-i9 alkaryl, Ci_i2-alkyl, C2-12alcenilo, C ₂ -i2-alkynyl, Ci_i2-haloalkyl, C2-I2- haloalkenyl, C2-12haloalquinil, Ci_i2-alkoxy, Ci_i2-alkylthio, Ci_i2-holoalcóxi, C1-12haloalquiltio, _i2 _{C3-cycloalkyl,} C4-8-cycloalkenyl, Cs-s-cicloalquinil C ₃ _ ₈ cycloalkyloxy, C ₃ _8- cycloalkylthio, Cy-w-aralkyl, Cj-w-alkaryl; bicyclic C512-alkyl, C7-i2-alkenyl; where, in the cyclic ring system, one or more carbon atoms can be replaced by hetero atoms selected from the groups consisting of N, O, and S (O) _n ; and all of the groups mentioned above may be replaced by one or more groups selected from the group consisting of X, R ', OR', SR ', NR' ₂ , SiR ' ₃ , COOR', CN, and CONR '₂; or two R ^9s together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group Petition 870190078277, of 8/13/2019, p. 163/187 4/26 consisting of C (= O), C (= S), S (O) _m and SiR'2 can form a four to ten membered ring, which can in turn be replaced by one or more X , R ', OR', SR ', NR' ₂ , SiR ' ₃ , COOR', CN, and CONR '₂; and where all groups of R ⁸ and R ⁹ can be optionally substituted by one or more groups selected from the group consisting of X, R ', OR', SR ', NR' ₂ , SíR ' ₃ , COOR', CN, and CONR '₂; Where X represents halogen; Where R 'represents hydrogen, Ci_i _{2 q} _ i UII straight chain or branched , or C ₃ _ 10 cyclic alkyl, which is optionally substituted by one or more X; R represents hydrogen; NR _'2, OR', Ci_i ₂ -alkyl, straight or branched chain Ci_i ₂ -haloalquil, _C3 _8 cyclic alkyl are optionally substituted by one or more groups selected from groups formed by X, R ', OR ', SR', NR ' ₂ , SiR' ₃ , COOR ', CN, and CONR' ₂ , C ₅ -i ₈ -aryl, which is optionally substituted by one or more R '; where, men represent integers where n = 0, 1 or 2; and m = I or 2; and agronomically acceptable salts, metal complexes, structural isomers / isomers, stereoisomers, diastereoisomers, enantiomers, tautomers or N-oxides of said compounds. 2. A compound of general formula (I) according to claim 1, characterized by the fact that each substituent is independently selected from: R ¹ is hydrogen, Ci_6-alkyl, Ci_6-alkoxy, Ci_6.alquiltio, Ci_6-haloalkyl, _C3 _8cicloalquill; R ² and R ³ are Ci_6-alkyl, C2 _6 alkenyl, C2 _6- alkynyl, Ci_6-alkoxy, C1-6alkylthio, Ci_6-haloalkyl, _C3 _8 cycloalkyl; Petition 870190078277, of 8/13/2019, p. 164/187 5/26 R ¹ and R ² , R ² and R ³ or R ¹ and R ³ together with the atoms to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) _m and SiR'2 can form a ring of four to seven members, which, in turn, can be replaced by one or more X, R ', OR', SR ', NR'2, SiR'3, COOR', CN, and CONR '₂; R ⁴ and R ⁵ are X, CN, S (O) _n R NR'R ' , (C = O) -R, CR' = NR CI_ ₆ alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6-haloalkyl, C1-6-haloalkylthio, C3-8cycloalkyl, C3-8-cycloalkylthio; R ⁶ and R ⁷ are hydrogen, X, CN, S (O) _n R, NR'R, (C = O) -R, CR '= NR, C1-6-alkyl, C2-6-alkenyl, C2-6 -alkynyl, C1-6-haloalkyl, C1-6-haloalkylthio, C3-8-cycloalkyl, Cs-s-cycloalkylthio; R ⁴ and R ⁷ or R ⁵ and R ⁶ together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) _m and SiR'2 can form a four to seven membered ring, which in turn can be replaced by one or more X, R ', OR', SR ', NR' ₂ , SiR ' ₃ , COOR', CN, and CONR '₂; R ⁸ is hydrogen, -CN, -S (O) _n R, NR'R ' , (C = O) -R, CR' = NR CI_ ₆ alkyl, C2-6 alkenyl, C2-6 alkynyl, Ci_6- haloalkyl, C3-8-cycloalkyl, C3-8 heterocyclic, Cvs-alkylheterocyclic; R ⁹ is X, CN, SCN, SF ₅ , R, OR, NO ₂ , NR ₂ , SíR ' ₃ , (C = O) -R, S (O) _n R, OS (O) _n R, OSiR' _3, NR'S (O) _n R ₈ CI_ -alkyl-S (O) _n R, CI_ ₆ -alkyl- (C = O) R, -NR COR, C2-6-alkenyl, C2-6-alkynyl, Ci_6 -haloalkyl, C2-6-haloalkenyl, C1-2-alkoxy, C1-2-alkylthio, C1-2-holoalkoxy, C1-2-haloalkylthio, C3-8cycloalkyl, C4-8-cycloalkenyl, Cs-s-cycloalkyl or R-cycloalkyl, or cycloalkyl, or ⁹ together with the atom to which they are attached or together with Petition 870190078277, of 8/13/2019, p. 165/187 6/26 other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) _m and SiR'2 can form a four to ten-membered ring which in turn can be replaced by one or more X, R ', OR', SR ', NR' ₂ , SiR ' ₃ , COOR', CN, and CONR '₂; An isphenyl, naphthalenyl, furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidyl, benzyl, benzyl, pyrimidyl, benzyl, pyrimidine benzoxazolyl, quinolinyl, isoquinolinyl, iquinazolinyl, cinonyl; replaced with one or more R ⁹ ; where R ¹ to R ⁹ can be optionally substituted by one or more groups selected from the group consisting of X, R, OR ', SR', NR ' ₂ , SiR' ₃ , COOR ', CN, and CONR'₂; and agronomically acceptable salts isomers / structural isomers, stereoisomers, diastereoisomers, enantiomers, tautomers or N-oxides of said compounds A compound of general formula (I) according to claim 1, 2 or 4, characterized by the fact that each substituent is independently selected from: R ¹ is hydrogen or C 1-6 alkyl; R ² and R ³ are C1-6 alkyl, C1-6 haloalkyl; R ⁴ and R ⁵ are X, CN, Ci_6-alkyl, Ci_6-haloalkyl, _C3 _8-cicloalquill; R ⁶ and R ⁷ are hydrogen, X, C1-6 alkyl, C1-6 haloalkyl; R ⁸ is hydrogen, -CN, -S (O) _n R, (C = O) -R, Ci_6-alkyl, Ci_6-haloalkyl, _C2 _6alcenilo, C2 _6-alkynyl, _C3 _8 cycloalkyl, _C3 _6- heterocyclic, C ₃ -6-alkyletherocyclic; R ⁹ is X, CN, SCN, SF ₅ , R, OR, NOZ, NR ₂ , SíR ' ₃ , (C = O) -R, S (O) _n R, Ci_ ₆ -alkyl-S (O) _n R, OS (O) _n R, OSiR ' ₃ , NR'S (O) _n R, Ci_ ₆ -alkyl- (C = O) Petition 870190078277, of 8/13/2019, p. 166/187 7/26 R, CR, NR, SCi_6-alkyl, Ci-O-alkenyl, C-O-alkynyl, Ci_6-haloalkyl, C2-6haloalcenilo, Ci_i2-alkoxy, Ci_i2-alkylthio, Ci_i2-holoalcóxi, C1-12haloalquiltio, C ₃ _8- cycloalkyl, C4-8-cycloalkenyl, _C3 _8-cycloalkyloxy, C3-8cicloalquiltio, or two R ⁹ together with the atom to which they are attached or in conjunction with other atom selected from the group consisting of C, N, O, S and including optionally, 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) _m and SiR 2 can form a four to ten member ring which in turn can be replaced by one or more X, R ', OR', SR ', NR' ₂ , SiR ' ₃ , COOR', CN, and CONR '₂; An isphenyl, naphthalenyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl isoxazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl and quinolinyl; replaced with one or more R ⁹ ; where R ¹ to R ⁹ can be optionally substituted by one or more groups selected from the group consisting of X, R, OR ', SR', NR'2, SiR ' ₃ , COOR', CN, and CONR '₂; and agronomically acceptable salts isomers / structural isomers, stereoisomers, diastereoisomers, enantiomers, tautomers or N-oxides of said compounds. A compound according to any one of claims 1, 2, or 3, characterized by the fact that the compounds of general formula (I) are: N '- (2,5-dimethyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2,5-dimethyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-5-methyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (N-phenyl-methyl-sulfonamide) phenyl) -N-ethyl-Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 167/187 8/26 N '- (2,5-dimethyl-4- (methyl (2-methyl-4- (perfluoropropane-2yl) phenyl) amino) phenyl) -N-ethyl-N-methylformimidamide; N '- (4 - ((4-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((3,4-dichlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- (methyl (3,4,5-trifluorophenyl) amino) phenyl) -N-ethyl-N methylformimidamide; Ν'- (2-chloro-5-methyl-4- (methyl (m-tolyl) amino) phenyl) -N-ethyl-N methylformimidamide; N '- (2-chloro-4 - ((3,4-dichlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (p-tolyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((2-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- (N-phenyl-methyl-sulfonamide) phenyl) -N-ethyl-N methylformimidamide; N '- (2-chloro-4 - ((2-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((4-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 168/187 9/26 N '- (2-chloro-4 - ((4-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((4-methoxy-3-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3,4-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3,5-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (m-tolyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N-ethyl-N '- (4 - ((3-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (p-tolyl) amino) phenyl) -N-ethyl-N-methylformimidamide; N-ethyl-N '- (4 - ((4-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N-ethyl-N'- (4- ((3-methoxyphenyl) amino) -2,5-dimethylphenyl) -N methylformimidamide; N '- (2,5-dimethyl-4- (m-tolylamino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2,5-dimethyl-4- (p-tolylamino) phenyl) -N-ethyl-N-methylformimidamide; N '- (4 - ((4- (tert-butyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((4- (tert-butyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((2-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((2-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 169/187 10/26 N-ethyl-N '- (4 - ((2-fluorophenyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N-ethyl-N '- (4 - ((2-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N '- (2-chloro-4 - ((2-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N-ethyl-N '- (4 - ((3-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N-ethyl-N '- (4 - ((4-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N '- (4 - ((2-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N- (4 - ((((((methyl)) amino) methylene) amino) -2,5-dimethylphenyl) -Nphenylacetamide N '- (2-chloro-5-methyl-4- (methyl (pyridin-2-yl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((4-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N-ethyl-N '- (4 - ((4-fluorophenyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N-ethyl-N'- (4- ((2-methoxyphenyl) amino) -2,5-dimethylphenyl) -N methylformimidamide; N-ethyl-N '- (4 - ((3-fluorophenyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N '- (2-chloro-4 - ((2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 170/187 11/26 N- (3-chlorophenyl) -N, 2,5-trimethyl-4 - ((morpholinomethylene) amino) aniline N '- (2-chloro-4 - ((3-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N- (3-chlorophenyl) -N, 2,5-trimethyl-4 - (((piperidine-1-ylmethylene) amino) aniline N-allyl-N '- (4 - ((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N '- (4 - ((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-isopropyl-Nmethylformimidamide; N '- (4 - ((2-bromophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((3-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N-ethyl-Ν'- (4- ((4-methoxyphenyl) amino) -2,5-dimethylphenyl) -N methylformimidamide; N '- (2,5-dimethyl-4 - ((2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 171/187 12/26 N '- (2,5-dimethyl-4 - ((3- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((2-bromophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N-ethyl-N '- (4 - ((2-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (3- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- ((3 - (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- (m-tolylamino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-4 - ((3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- (o-tolylamino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-4 - ((4-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (o-tolylamino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-4 - ((4-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (o-tolyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((2-bromophenyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((2-bromophenyl) (methyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (o-tolyl) amino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2-chloro-4 - ((2-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 172/187 13/26 Ν'- (2-chloro-5-methyl-4- ((2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylform i m i da m i da; Ν'- (2-chloro-5-methyl-4- ((4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((4-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((4-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- ((3 - (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((2,6-difluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((2,6-difluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((2,6-difluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 173/187 14/26 N '- (2-chloro-4 - ((2,6-difluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((2-chloro-6-fluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((2-chloro-6-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((2-chloro-6-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylform i m i da m i da; N '- (2,5-dimethyl-4 - ((4- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((2,6-dichloro-4- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethylN-methylformimidamide; N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- ((3 - (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- ((4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethylN-methylformimidamide; N '- (2,5-dimethyl-4- (methyl (4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 174/187 15/26 N '- (2-chloro-5-methyl-4- (methyl (4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethylN-methylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethylN-methylformimidamide; Ν'- (2-chloro-5-methyl-4- (N-phenylethylsulfonamido) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((2,4-dichloro-6- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -Netyl-N-methylformimidamide; N '- (2-chloro-5-methyl-4 - (((4- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide; N '- (2-chloro-4 - ((2-chloro-6-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (4- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (4- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) N-ethyl-N-methylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (3- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((2 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- ((2- ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((3 - ((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((4 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- ((4- ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N methylformimidamide; Petition 870190078277, of 8/13/2019, p. 175/187 16/26 N '- (2,5-dimethyl-4- (methyl (2 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (2 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethylN-methylformimidamide; N '- (2,5-dimethyl-4- (methyl (4 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (4 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethylN-methylformimidamide; N '- (4 - ((3 - ((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((3 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((4- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4 - ((4- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (3 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (3 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethylN-methylformimidamide; N '- (2,5-dimethyl-4- (methyl (4- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (4- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((3- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4 - (((3- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide; Petition 870190078277, of 8/13/2019, p. 176/187 17/26 N '- (2,5-dimethyl-4- (methyl (3- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) -Netyl-N-methylformimidamide; N '- (2-chloro-5-methyl-4- (methyl (3- (pentafluoro-16-sulfanyl) phenyl) amino) phenyl) N-ethyl-N-methylformimidamide; N '- (4 - ((3,5-bis (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((3,5-bis (trifluoromethyl) phenyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- ((3 - ((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N methylformimidamide; N '- (2-chloro-4 - ((4- (dimethylamino) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((4- (dimethylamino) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3 - ((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3 - ((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -Netyl-N-methylformimidamide; N '- (4 - ((3- (difluoromethoxy) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((3- (difluoromethoxy) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3- (difluoromethoxy) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 177/187 18/26 N '- (2,5-dimethyl-4 - ((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((4- (difluoromethoxy) phenyl) (methyl) amino) -5-methylphenyl) -N-ethylN-methylformimidamide; N '- (4 - ((2,5-difluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((2,5-difluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((3,5-bis (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethylN-methylformimidamide; N '- (4 - ((3,5-bis (trifluoromethyl) phenyl) (methyl) amino) -2-chloro-5-methylphenyl) -Netyl-N-methylformimidamide; N '- (2,5-dimethyl-4 - ((5-methyl-2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Ν'- (4 - ((2,5-difluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N methylformimidamide; N '- (2-chloro-4 - ((2,5-difluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (5-methyl-2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethylN-methylformimidamide; N '- (4 - ((4-chloro-2- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((4-chloro-2- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethylN-methylformimidamide; Ν'- (4 - ((4-chloro-2- (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -Netyl-N-methylformimidamide; N '- (2-chloro-4 - ((4-chloro-2- (trifluoromethyl) phenyl) (methyl) amino) -5-methylphenyl) N-ethyl-N-methylformimidamide; Petition 870190078277, of 8/13/2019, p. 178/187 19/26 N '- (2-chloro-5-methyl-4- (methyl (2- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3- (difluoromethoxy) phenyl) (methyl) amino) -5-methylphenyl) -N-ethylN-methylformimidamide; Ν'- (2-chloro-5-methyl-4- ((2- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((2-chloro-4- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((2-chloro-4- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethylN-methylformimidamide; Ν'- (4 - ((2-chloro-4- (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -Netyl-N-methylformimidamide; N '- (2-chloro-4 - ((2-chloro-4- (trifluoromethyl) phenyl) (methyl) amino) -5-methylphenyl) N-ethyl-N-methylformimidamide; N '- (2,5-dimethyl-4 - ((2- (methylthio) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N-ethyl-Ν'- (4- ((4-fluoro-3 - (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -2,5 dimethylphenyl) -N-methylformimidamide; N '- (2-chloro-4 - ((4-fluoro-3- (1,1, 2,2-tetrafluoroethoxy) phenyl) amino) -5methylphenyl) -N-ethyl-N-methylformimidamide; 5-chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4 - ((morpholinomethylene) amino) aniline N '- (2-chloro-4- (N- (2-fluorophenyl) methylsulfonamido) -5- methylphenyl) -N-ethyl-Nmethylformimidamide; N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2fluorophenyl) acetamide N '- (2-chloro-4 - ((2-fluorophenyl) (methyl) amino) -5-methylphenyl) -N, Ndimethylformimidamide; Petition 870190078277, of 8/13/2019, p. 179/187 20/26 N '- (2-chloro-4- (ethyl (2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; 5-chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4 - ((morpholinomethylene) amino) aniline 5-chloro-N - (2-fluorophenyl) -N, 2-dimethyl-4 ((thiomorpholinomethylene) amino) aniline N-ethyl-N '- (5-fluoro-4 - (((4-fluoro-3- (1,1, 2,2-tetrafluoroethoxy) phenyl) amino) -2methylphenyl) -N-methylformimidamide; N-ethyl-N '- (5-fluoro-4 - ((4-fluoro-3- (1,2,2,2tetrafluoroethoxy) phenyl) (methyl) amino) -2-methylphenyl) -N-methylformimidamide; N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2chlorophenyl) acetamide; N '- (2-chloro-4- (N- (2-chlorophenyl) methylsulfonamido) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((4 - ((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((4 - ((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((4 - ((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((4 - ((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -Netyl-N-methylformimidamide; N '- (2-chloro-4- (ethyl (phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -Nphenylacetamide; N '- (2-chloro-4 - ((2 - ((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 180/187 21/26 N '- (2-chloro-4 - ((2 - ((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -Netyl-N-methylformimidamide; N '- (2-chloro-4- (ethyl (3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3- (difluoromethoxy) -4-fluorophenyl) amino) -5-methylphenyl) -Netyl-N-methylformimidamide; Ν'- (2-chloro-4- (N- (3-methoxyphenyl) methylsulfonamido) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((3- (difluoromethoxy) -4-fluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((3- (difluoromethoxy) -4-fluorophenyl) (methyl) amino) -5methylphenyl) -N-ethyl-N-methylformimidamide; N '- (4 - ((3- (difluoromethoxy) -4-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -Netyl-N-methylformimidamide; N '- (4 - ((2,5-dimethylphenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((2,5-dimethylphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2chlorophenyl) propionamide; N-ethyl-N '- (5-fluoro-4 - ((4-methoxyphenyl) amino) -2-methylphenyl) -Nmethylformimidamide; N-ethyl-N '- (5-fluoro-4 - ((4-methoxyphenyl) (methyl) amino) -2-methylphenyl) -Nmethylformimidamide; N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2fluorophenyl) propionamide Petition 870190078277, of 8/13/2019, p. 181/187 22/26 N '- (2-chloro-4- (N- (4-fluoro-3- (1,2,2,2tetrafluoroethoxy) phenyl) methylsulfonamido) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4 - ((3- (1,1, 2,2-tetrafluoroethoxy) phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2,5-dimethyl-4- (methyl (3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) phenyl) -Netyl-N-methylformimidamide; N-ethyl-N '- (4 - ((2-fluoro-5-methylphenyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N-ethyl-N '- (5-fluoro-4 - ((2-fluorophenyl) amino) -2-methylphenyl) -Nmethylformimidamide; N-ethyl-N '- (4 - ((2-fluoro-5-methylphenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N '- (2-chloro-4 - ((2-fluoro-5-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; N-ethyl-N '- (5-fluoro-2-methyl-4- (phenylamino) phenyl) -N-methylformimidamide; N '- (4 - ((2-chlorophenyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((4- (tert-butyl) phenyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-Nmethylformimidamide; N-ethyl-N '- (5-fluoro-2-methyl-4- (m-tolylamino) phenyl) -N-methylformimidamide; N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -Nphenylpropionamide; N- (5-chloro-4 - (((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (3methoxyphenyl) acetamide; N '- (2-chloro-4 - (((4-fluoro-3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 182/187 23/26 N-ethyl-N '- (4 - ((4-fluoro-3-methoxyphenyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N-ethyl-N '- (4 - ((4-fluoro-3-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -Nmethylformimidamide; N '- (4 - ((2 - ((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (4 - ((2 - ((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-4 - ((4-fluoro-3-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethylN-methylformimidamide; N '- (2-bromo-6-fluoro-3-methyl-4- (phenylamino) phenyl) -N-ethyl-Nmethylformimidamide; N '- (2-chloro-5-methyl-4 - (((5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl) amino) phenyl) N-ethyl-N-methylformimidamide; N '- (2-bromo-6-fluoro-3-methyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- ((1-methylindoline-5-yl) amino) phenyl) -N-ethyl-N methylformimidamide; N '- (2,5-dimethyl-4 - (((5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl) amino) phenyl) -Netyl-N-methylformimidamide; N-ethyl-N '- (5-fluoro-2-methyl-4- (methyl (phenyl) amino) phenyl) -Nmethylformimidamide; N '- (4 - ((4- (tert-butyl) phenyl) (methyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-Nmethylformimidamide; N-ethyl-N '- (5-fluoro-2-methyl-4- (methyl (m-tolyl) amino) phenyl) -Nmethylformimidamide; N-ethyl-N '- (7 - ((2-methoxyphenyl) amino) -2,3-dihydro-1H-indeno-4-yl) -Nmethylformimidamide; Petition 870190078277, of 8/13/2019, p. 183/187 24/26 N-ethyl-N-methyl-N'- (7- (p-tolylamino) -2,3-dihydro-1 H-indene-4yl) formimidamide; N '- (7 - ((4-chlorophenyl) amino) -2,3-dihydro-1H-indeno-4-yl) -N-ethyl-Nmethylformimidamide; N-ethyl-N-methyl-N '- (4- (phenylamino) naphthalene-1-yl) formimidamide; N '- (2,5-dimethyl-4- (pyridine-2-ylamino) phenyl) -N-ethyl-N-methylformimidamide; N '- (2,5-dimethyl-4- (methyl (pyridine-2-yl) amino) phenyl) -N-ethyl-Nmethylformimidamide; Ν'- (2-chloro-5-methyl-4- (pyridine-2-ylamino) phenyl) -N-ethyl-N methylformimidamide; 5. Composition to control or prevent phytopathogenic microorganisms, characterized by the fact that it comprises a compound of general formula (I), as defined in any one of claims 1 to 5 and one or more inert vehicles. 6. Compositions characterized by the fact that they comprise compounds of general formula (I) as defined in any one of claims 1 to 5 and / or one or more compatible compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, regulators of plant growth, antibiotics, fertilizers and / or mixtures thereof. Compositions according to claim 5 or 6, characterized in that the concentration of compounds of the general formula (I) varies from 1 to 90% by weight, in relation to the total weight of the composition, preferably from 5 to 50% by weight, based on the total weight of the composition. 8. Use of compounds of general formula (I) as defined in any of claims 1 to 4, characterized by the fact that it is for the control of phytopathogenic fungi, bacteria, insects, nematodes, Petition 870190078277, of 8/13/2019, p. 184/187 25/26 mites from agricultural crops and or horticultural crops. 9. Use of compounds of general formula (I) as defined in any of claims 1 to 4, or compositions as defined in any of claims 5 to 7, characterized by the fact that it is to control or prevent phytopathogenic fungi from cultures agricultural and / or horticultural crops. 10. Use of the compositions as defined in any of claims 5 to 7, characterized by the fact that it is to control or prevent phytopathogenic fungi, bacteria, insects, nematodes, mites from agricultural crops and or horticultural crops. 11. Use of compounds of general formula (I) as defined in any of claims 1 to 4 or compositions as defined in any of claims 5 to 7, characterized by the fact that the agricultural crops are cereals, corn, rice, soybeans and other legumes, fruit and fruit trees, walnuts and walnuts, citrus fruits and citrus trees, any vegetable plants, cucurbits, oil plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato , onions, peppers and other vegetables, and ornamentals. 12. Method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and / or horticultural crops, characterized by the fact that a compound of general formula (I) as defined in any of claims 1 to 4 or compositions such as defined in any one of claims 5 to 7, is applied to the plants, their parts or their location. 13. Method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and / or horticultural crops, characterized by the fact that a compound of general formula (I) as defined in any one of claims 1 to 4 Petition 870190078277, of 8/13/2019, p. 185/187 26/26 or compositions as defined in any one of claims 5 to 7, is applied to plant seeds. 14. Method of controlling or preventing phytopathogenic microorganisms in agricultural crops and / or horticultural crops, characterized by the fact that it uses the compounds of general formula (I) as defined in any one of claims 1 to 4 or compositions as defined in any of the claims 5 to 7, which consists of applying effective dosages of compounds or compositions in quantities ranging between 1 g and 5 kg per hectare of agricultural or horticultural crops.